488-59-5

Basic information

• Product Name: SCYLLO-INOSITOL
• Synonyms: 1,3,5/2,4,6-HEXAHYDROXYCYCLOHEXANE;COCOSITOL;Inositol, scyllo-;QUERCINITOL;SCYLLITO;SCYLLITOL;SCYLLO-INOSITOL;Scyllitol, Cocositol, Quercinitol,1,3,5/2,4,6-Hexahydroxycyclohexane
• CAS NO: 488-59-5
• Molecular Formula: C₆H₁₂O₆
• Molecular Weight: 180.16
• EINECS: 200-258-5
• Product Categories: All Inositols;Biochemistry;Sugars;Vitamin Related Compounds;Vitamins;Inositols;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 488-59-5.mol
• Article Data: 22

Chemical Properties

• Melting Point: 350 °C
• Boiling Point: 291.3°Cat760mmHg
• Flash Point: 143.4°C
• Appearance: /
• Density: 2.038±0.06 g/cm3 (20 ºC 760 Torr)
• Refractive Index: 0 ° (C=1, H2O)
• Storage Temp.: -20°C Freezer
• Solubility: Methanol (Slightly), Water (Slightly)
• PKA: 12.63±0.70(Predicted)
• Water Solubility: 10.1g/L(18 oC)
• CAS DataBase Reference: SCYLLO-INOSITOL(CAS DataBase Reference)
• NIST Chemistry Reference: SCYLLO-INOSITOL(488-59-5)
• EPA Substance Registry System: SCYLLO-INOSITOL(488-59-5)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 488-59-5(Hazardous Substances Data)

Usage

Description

Scyllo-Inositol, also known as cyclohexane-1,2,3,4,5,6-hexol, is a white crystalline solid that belongs to the cyclohexanehexol family. It is a naturally occurring isomer of inositol and has been found to have various applications in the pharmaceutical and healthcare industries.

Uses

Used in Pharmaceutical Industry:
Scyllo-Inositol is used as a therapeutic agent for the treatment of amyotrophic lateral sclerosis (ALS), a progressive neurodegenerative disease that affects nerve cells in the brain and spinal cord. It helps in managing the symptoms and slowing down the progression of the disease.
Used in Alzheimer's Treatment:
Scyllo-Inositol is also used as an anti-Alzheimer's agent, a neurodegenerative disorder characterized by memory loss, cognitive decline, and behavioral changes. It has been shown to have potential benefits in improving cognitive function and reducing the severity of Alzheimer's symptoms.

InChI:InChI=1/C6H12O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-12H/t1-,2+,3-,4+,5-,6+

Synthetic route

(1R,3S,5S,6R,7S,8S,9S)-2,4,10-trioxatricyclo<3.3.1.13,7>decane-6,8,9-triol → myo-inositol (488-59-5)

Conditions	Yield
With water; trifluoroacetic acid at 20℃; for 1h;	94%
With trifluoroacetic acid for 2h;
With trifluoroacetic acid In water

1-O-benzoyl-scyllo-inositol (261621-51-6) → myo-inositol (488-59-5)

Conditions	Yield
With sodium methylate In methanol for 3h; Hydrolysis; Heating;	88%

1-O-allyl-2,5-di-O-benzyl-scyllo-inositol → myo-inositol (488-59-5)

Conditions	Yield
Stage #1: 1-O-allyl-2,5-di-O-benzyl-scyllo-inositol With methanol; 10percent Pd/C for 6h; Heating; Stage #2: With hydrogenchloride at 80℃; Stage #3: With hydrogen; 10percent Pd/C In methanol; water for 12h; Further stages.;	85%

Penta-O-acetyl-myo-inosose (20097-56-7) → myo-inositol (488-59-5)

Conditions	Yield
With sodium tetrahydroborate In methanol for 0.5h; Ambient temperature;	78%

benzenehexol (608-80-0) → myo-inositol (488-59-5)

Conditions	Yield
With ethanol; nickel at 125℃; under 95616 Torr; Hydrogenation;

1,2:4,5-Dianhydro-epi-inositol (50473-98-8) → neo-inositol (488-54-0) + myo-inositol (488-59-5) + chiro-inositol (18685-70-6)

Conditions	Yield
With sulfuric acid for 3h; Heating;	A 15 % Spectr. B 5 % Spectr. C 80 % Spectr.

1,2:4,5-Dianhydro-muco-inosit (50473-95-5, 50473-98-8, 50473-99-9, 50474-02-7, 50474-08-3) → D-myo-inositol (87-89-8) + muco-inositol (488-55-1) + myo-inositol (488-59-5) + chiro-inositol (18685-70-6)

Conditions	Yield
With sulfuric acid for 3h; Heating;	A 0.5 % Spectr. B 80 % Spectr. C 0.5 % Spectr. D 19 % Spectr.

D-myo-inositol (87-89-8) → myo-inositol (488-59-5)

Conditions	Yield
nickel In water for 24h; Heating; Yield given;
Stage #1: D-myo-inositol; lyo Acetobactor Species In water at 28℃; under 1018.63 Torr; for 120h; pH=~ 4 - 7; Enzymatic reaction; Industry scale; Stage #2: With sodium hydroxide In water at 120 - 125℃; for 0.166667h; pH=12 - 13; Product distribution / selectivity; Industry scale;

scyllo-inosose → D-myo-inositol (87-89-8) + myo-inositol (488-59-5)

Conditions	Yield
With sodium amalgam; acetic acid Trennung von dem Stereoisomeren ueber das Hexaacetyl-Derivat;
With water; platinum Hydrogenation;

(1S,2S,3R,4S,5R,6R)-4,5,6-Tris-benzyloxy-cyclohexane-1,2,3-triol → myo-inositol (488-59-5)

Conditions	Yield
With hydrogen; palladium dihydroxide In methanol at 20℃; for 24h;	18.4 mg

(+)-(1S,2R,3R,4S)-1,4-diacetoxy-2,3-dibromocyclohex-5-ene (170210-89-6) → myo-inositol (488-59-5)

Conditions

Yield

Multi-step reaction with 5 steps 1.1: 80 percent / sodium / tetrahydrofuran / 13 h / 0 - 20 °C 2.1: 71 percent / aq. H2O2; trifluoroacetic anhydride; Na2CO3 / CH2Cl2 / 3 h / 20 °C 3.1: 96 percent / PPTS / acetone / 16 h / 20 °C 4.1: sodium / 24 h / 90 °C 4.2: 60 percent / aq. HCl / tetrahydrofuran / 20 °C 5.1: methanol / 10percent Pd/C / 6 h / Heating 5.2: aq. HCl / 80 °C 5.3: 85 percent / H2 / 10percent Pd/C / methanol; H2O / 12 h View Scheme

(1R,2S,3S,4R)-1,4-di-O-benzylconduritol B (594858-42-1) → myo-inositol (488-59-5)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 71 percent / aq. H2O2; trifluoroacetic anhydride; Na2CO3 / CH2Cl2 / 3 h / 20 °C 2.1: 96 percent / PPTS / acetone / 16 h / 20 °C 3.1: sodium / 24 h / 90 °C 3.2: 60 percent / aq. HCl / tetrahydrofuran / 20 °C 4.1: methanol / 10percent Pd/C / 6 h / Heating 4.2: aq. HCl / 80 °C 4.3: 85 percent / H2 / 10percent Pd/C / methanol; H2O / 12 h View Scheme

2,3-anhydro-1,4-di-O-benzyl-myo-inositol (594858-43-2) → myo-inositol (488-59-5)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 96 percent / PPTS / acetone / 16 h / 20 °C 2.1: sodium / 24 h / 90 °C 2.2: 60 percent / aq. HCl / tetrahydrofuran / 20 °C 3.1: methanol / 10percent Pd/C / 6 h / Heating 3.2: aq. HCl / 80 °C 3.3: 85 percent / H2 / 10percent Pd/C / methanol; H2O / 12 h View Scheme

1,2-anhydro-3,6-di-O-benzyl-4,5-di-O-isopropyl-myo-inositol → myo-inositol (488-59-5)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium / 24 h / 90 °C 1.2: 60 percent / aq. HCl / tetrahydrofuran / 20 °C 2.1: methanol / 10percent Pd/C / 6 h / Heating 2.2: aq. HCl / 80 °C 2.3: 85 percent / H2 / 10percent Pd/C / methanol; H2O / 12 h View Scheme

4,6-di-O-tosyl-myo-inositol 1,3,5-orthoformate → myo-inositol (488-59-5)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: 1.99 g / Me2SO; oxalyl chloride / CH2Cl2 / 1 h / -78 °C 2.1: 99 percent / sodium borohydride / methanol; tetrahydrofuran / 0.5 h / 20 °C 3.1: MeONa / methanol / 12 h / Heating 3.2: 98 percent / pyridine / 24 h / 20 °C 4.1: 98 percent / iso-butylamine / methanol / 12 h / Heating 5.1: 94 percent / trifluoroacetic acid; water / 1 h / 20 °C View Scheme

acetic acid 8,9-diacetoxy-2,4,10-trioxa-tricyclo[3.3.1.13,7]dec-6-yl ester → myo-inositol (488-59-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 98 percent / iso-butylamine / methanol / 12 h / Heating 2: 94 percent / trifluoroacetic acid; water / 1 h / 20 °C View Scheme

2,4-di-O-tosyl-scyllo-inositol 1,3,5-orthoformate → myo-inositol (488-59-5)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: MeONa / methanol / 12 h / Heating 1.2: 98 percent / pyridine / 24 h / 20 °C 2.1: 98 percent / iso-butylamine / methanol / 12 h / Heating 3.1: 94 percent / trifluoroacetic acid; water / 1 h / 20 °C View Scheme

C21H20O10S2 → myo-inositol (488-59-5)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 99 percent / sodium borohydride / methanol; tetrahydrofuran / 0.5 h / 20 °C 2.1: MeONa / methanol / 12 h / Heating 2.2: 98 percent / pyridine / 24 h / 20 °C 3.1: 98 percent / iso-butylamine / methanol / 12 h / Heating 4.1: 94 percent / trifluoroacetic acid; water / 1 h / 20 °C View Scheme

Benzoic acid (1R,3R,5R,6R,7S,8R,9S)-8,9-bis-(toluene-4-sulfonyloxy)-2,4,10-trioxa-tricyclo[3.3.1.13,7]dec-6-yl ester → myo-inositol (488-59-5)

Conditions

Yield

Multi-step reaction with 6 steps 1.1: 2.01 g / iso-butylamine / methanol / 12 h / Heating 2.1: 1.99 g / Me2SO; oxalyl chloride / CH2Cl2 / 1 h / -78 °C 3.1: 99 percent / sodium borohydride / methanol; tetrahydrofuran / 0.5 h / 20 °C 4.1: MeONa / methanol / 12 h / Heating 4.2: 98 percent / pyridine / 24 h / 20 °C 5.1: 98 percent / iso-butylamine / methanol / 12 h / Heating 6.1: 94 percent / trifluoroacetic acid; water / 1 h / 20 °C View Scheme

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside (53008-65-4) → myo-inositol (488-59-5)

Conditions	Yield
Multi-step reaction with 6 steps 1: N,N-dicyclohexylcarbodiimide; trifluoroacetic acid; pyridine / dimethylsulfoxide; benzene / 24 h / 20 °C 2: Et3N; 4-(dimethylamino)pyridine / 1,2-dichloro-ethane / 3 h / Heating 3: PdCl2 / dioxane; H2O / 3 h / 60 °C 4: NaBH4 / methanol / 0.5 h / 0 °C 5: NaOH / methanol / 12 h / 20 °C 6: 18.4 mg / H2 / Pd(OH)2/C / methanol / 24 h / 20 °C View Scheme
Multi-step reaction with 6 steps 1: N,N-dicyclohexylcarbodiimide; trifluoroacetic acid; pyridine / dimethylsulfoxide; benzene / 24 h / 20 °C 2: Et3N; 4-(dimethylamino)pyridine / 1,2-dichloro-ethane / 3 h / Heating 3: PdCl2 / dioxane; H2O / 3 h / 60 °C 4: NaBH4 / methanol / 0.5 h / 0 °C 5: NaOH / methanol / 12 h / 20 °C 6: 18.4 mg / H2 / Pd(OH)2/C / methanol / 24 h / 20 °C View Scheme

methyl 6-aldehydo-2,3,4-tri-O-benzyl-α-D-glucopyranoside (83051-88-1) → myo-inositol (488-59-5)

Conditions	Yield
Multi-step reaction with 5 steps 1: Et3N; 4-(dimethylamino)pyridine / 1,2-dichloro-ethane / 3 h / Heating 2: PdCl2 / dioxane; H2O / 3 h / 60 °C 3: NaBH4 / methanol / 0.5 h / 0 °C 4: NaOH / methanol / 12 h / 20 °C 5: 18.4 mg / H2 / Pd(OH)2/C / methanol / 24 h / 20 °C View Scheme
Multi-step reaction with 5 steps 1: Et3N; 4-(dimethylamino)pyridine / 1,2-dichloro-ethane / 3 h / Heating 2: PdCl2 / dioxane; H2O / 3 h / 60 °C 3: NaBH4 / methanol / 0.5 h / 0 °C 4: NaOH / methanol / 12 h / 20 °C 5: 18.4 mg / H2 / Pd(OH)2/C / methanol / 24 h / 20 °C View Scheme

(1R,2S,3S,4R,5S)-3,4,5-tribenzyloxy-2-hydroxy-6-oxocyclohexyl acetate (137893-52-8) → myo-inositol (488-59-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: NaBH4 / methanol / 0.5 h / 0 °C 2: NaOH / methanol / 12 h / 20 °C 3: 18.4 mg / H2 / Pd(OH)2/C / methanol / 24 h / 20 °C View Scheme

(E)-methyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-gluco-hex-5-enopyranoside (137793-91-0) → myo-inositol (488-59-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: PdCl2 / dioxane; H2O / 3 h / 60 °C 2: NaBH4 / methanol / 0.5 h / 0 °C 3: NaOH / methanol / 12 h / 20 °C 4: 18.4 mg / H2 / Pd(OH)2/C / methanol / 24 h / 20 °C View Scheme

(Z)-methyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-gluco-hex-5-enopyranoside (137793-90-9) → myo-inositol (488-59-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: PdCl2 / dioxane; H2O / 3 h / 60 °C 2: NaBH4 / methanol / 0.5 h / 0 °C 3: NaOH / methanol / 12 h / 20 °C 4: 18.4 mg / H2 / Pd(OH)2/C / methanol / 24 h / 20 °C View Scheme

D-1-O-acetyl-3,4,5-tri-O-benzyl-scyllo-inositol (220198-36-7) → myo-inositol (488-59-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaOH / methanol / 12 h / 20 °C 2: 18.4 mg / H2 / Pd(OH)2/C / methanol / 24 h / 20 °C View Scheme

methanol (67-56-1) + sodium tetrahydroborate (16940-66-2) → Trimethyl borate (121-43-7) + myo-inositol (488-59-5)

Conditions	Yield
With sulfuric acid with concd. H2SO4;
With H2SO4; scyllomyo-inosose with concd. H2SO4;

scyllo-inositol diborate-disodium salt complex → myo-inositol (488-59-5)

Conditions	Yield
With sulfuric acid; water at 36 - 43℃; for 5h; pH=2 - 3.5; Industry scale;
With hydrogenchloride; water at 85 - 95℃; Product distribution / selectivity;

D-myo-inositol (87-89-8) → 1L-chiro-inositol (38876-99-2) + neo-inositol (488-54-0) + myo-inositol (488-59-5)

Conditions	Yield
nickel In water at 95 - 100℃; Product distribution / selectivity;

1-O-β-D-glucopyranosyl-scyllo-inositol → alpha-D-glucopyranose (492-62-6) + myo-inositol (488-59-5)

Conditions	Yield
With cellobiase In aq. buffer at 40℃; for 20h; pH=7.0; Enzymatic reaction;

myo-inositol (488-59-5) + 4-Bromophenylboronic acid (5467-74-3) + water (7732-18-5) + potassium hydroxide → C18H14B2Br2O6(2-)*2K(1+)*3H2O

Conditions	Yield
for 1h; Reflux;	89%

myo-inositol (488-59-5) + 4-methylphenylboronic acid (5720-05-8) + sodium hydroxide (1310-73-2) → C20H20B2O6(2-)*2Na(1+)

Conditions	Yield
In water for 1h; Reflux;	89%

myo-inositol (488-59-5) + 4-methylphenylboronic acid (5720-05-8) + tetra(n-butyl)ammonium hydroxide (2052-49-5) → C20H20B2O6(2-)*2C16H36N(1+)

Conditions	Yield
In water for 1h; Reflux;	89%

myo-inositol (488-59-5) + (3-bromophenyl)boronic acid (89598-96-9) + water (7732-18-5) + potassium hydroxide → C18H14B2Br2O6(2-)*2K(1+)*5H2O

Conditions	Yield
for 1h; Reflux;	87%

myo-inositol (488-59-5) + water (7732-18-5) + potassium hydroxide + (2-bromophenyl)boronic acid (244205-40-1) → C18H14B2Br2O6(2-)*2K(1+)*4H2O

Conditions	Yield
for 1h; Reflux;	86%

butylboronic acid (4426-47-5) + myo-inositol (488-59-5) + potassium hydroxide → C14H24B2O6(2-)*2K(1+)

Conditions	Yield
In water for 1h; Reflux;	86%

myo-inositol (488-59-5) + orthoformic acid triethyl ester (122-51-0) → myo-Inositol orthoformate (98510-20-4)

Conditions	Yield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 100℃; for 22h; Inert atmosphere;	84%

myo-inositol (488-59-5) + water (7732-18-5) + 3,5-dibromophenylboronic acid + potassium hydroxide → C18H12B2Br4O6(2-)*2K(1+)*3H2O

Conditions	Yield
for 1h; Reflux;	84%

myo-inositol (488-59-5) + 4-methylphenylboronic acid (5720-05-8) + potassium hydroxide → C20H20B2O6(2-)*2K(1+)

Conditions	Yield
In water for 1h; Reflux;	84%
In water for 1h; Reflux;	84%

myo-inositol (488-59-5) + water (7732-18-5) + potassium hydroxide + phenylboronic acid (98-80-6) → C18H16B2O6(2-)*2K(1+)*3H2O

Conditions	Yield
for 1h; Reflux;	82%

myo-inositol (488-59-5) + n-octanoic acid chloride (111-64-8) → 1,2,3,4,5,6-all-trans-Hexakis(octanoyloxy)cyclohexane (98566-49-5)

Conditions	Yield
With trifluoroacetic acid for 2h; Ambient temperature;	74%

myo-inositol (488-59-5) + trimethyl orthoundecanoate → C17H30O6

Conditions	Yield
With toluene-4-sulfonic acid In toluene Inert atmosphere; Reflux;	71%

myo-inositol (488-59-5) + Dibenzyl N,N-diisopropylphosphoramidite (108549-23-1) → scyllo-inositol hexakis(dibenzyl phosphate)

Conditions	Yield
Stage #1: myo-inositol; Dibenzyl N,N-diisopropylphosphoramidite With 1H-tetrazole In N,N-dimethyl-formamide; acetonitrile at 20℃; for 24h; Stage #2: With dihydrogen peroxide In water; N,N-dimethyl-formamide; acetonitrile at 0 - 20℃; for 12h; pH=7; Aqueous sodium phosphate buffer;	55%
Stage #1: myo-inositol; Dibenzyl N,N-diisopropylphosphoramidite With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 24h; phosphorylation; Stage #2: With dihydrogen peroxide In phosphate buffer at 20℃; pH=7; Oxidation;	44%

myo-inositol (488-59-5) + N,N-diethyl-1,5-dihydro-3H-2,4,3-benzodioxaphosphepin-3-amine (82372-35-8) → hexa-O-(3-oxo-1,5-dihydro-3λ5-2,4,3-benzodioxaphosphepin-3-yl)-scyllo-inositol

Conditions	Yield
Stage #1: myo-inositol; N,N-diethyl-1,5-dihydro-3H-2,4,3-benzodioxaphosphepin-3-amine With 1H-tetrazole In dichloromethane at 20℃; Stage #2: With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 1h; Further stages.;	40%

myo-inositol (488-59-5) + benzyl bromide (100-39-0) → 1,3,4-tri-O-benzyl-myo-inositol

Conditions	Yield
Stage #1: myo-inositol; benzyl bromide With tetrabutylammomium bromide; di(n-butyl)tin oxide; N-ethyl-N,N-diisopropylamine In neat (no solvent) at 90℃; for 2.5h; Stage #2: With tetrabutylammomium bromide; di(n-butyl)tin oxide; N-ethyl-N,N-diisopropylamine In neat (no solvent) at 90℃; for 6.5h; regioselective reaction;	40%

C29H41ClN2O2 (937729-10-7) + myo-inositol (488-59-5) → AzIn

Conditions	Yield
Stage #1: C29H41ClN2O2; myo-inositol With pyridine In dichloromethane for 24h; Reflux; Inert atmosphere; Stage #2: In dichloromethane at 60℃; for 12h; Sealed flask; Large scale reaction;	19.6%

myo-inositol (488-59-5) → inositol (551-72-4, 643-12-9, 6917-35-7, 39907-99-8, 40461-73-2, 41546-32-1, 41546-33-2, 41546-34-3, 41546-35-4, 41546-36-5)

Conditions	Yield
With hydrogenchloride; acetic acid at 160℃; isoinositol;
With hydrogenchloride; acetic acid at 160℃; pseudoinositol;

myo-inositol (488-59-5) + acetic anhydride (108-24-7) → hexa-O-acetyl-isoinositol (20108-67-2, 29267-03-6)

Conditions	Yield
With zinc(II) chloride scyllitol hexaacetate;

Nonanoyl chloride (764-85-2) + myo-inositol (488-59-5) → 1,2,3,4,5,6-all-trans-Hexakis(nonanoyloxy)cyclohexane (88211-14-7)

Conditions	Yield
In trifluoroacetic acid Ambient temperature;

2-(pentylthio)acetic acid (22683-44-9) + myo-inositol (488-59-5) → Pentylsulfanyl-acetic acid 2,3,4,5,6-pentakis-(2-pentylsulfanyl-acetoxy)-cyclohexyl ester (136444-86-5)

Conditions	Yield
With trifluoroacetic acid for 18h; Ambient temperature;

5-Chlorovaleroyl chloride (1575-61-7) + myo-inositol (488-59-5) → 5-Chloro-pentanoic acid 2,3,4,5,6-pentakis-(5-chloro-pentanoyloxy)-cyclohexyl ester (129090-55-7)

Conditions	Yield
In trifluoroacetic acid Ambient temperature;

5-bromovaleroyl chloride (4509-90-4) + myo-inositol (488-59-5) → 5-Bromo-pentanoic acid 2,3,4,5,6-pentakis-(5-bromo-pentanoyloxy)-cyclohexyl ester (129090-56-8)

Conditions	Yield
In trifluoroacetic acid Ambient temperature;

6-bromohexanoyl chloride (22809-37-6) + myo-inositol (488-59-5) → 6-Bromo-hexanoic acid 2,3,4,5,6-pentakis-(6-bromo-hexanoyloxy)-cyclohexyl ester (129090-57-9)

Conditions	Yield
In trifluoroacetic acid Ambient temperature;

3-Butyloxypropanoic acid (7420-06-6) + myo-inositol (488-59-5) → 3-Butoxy-propionic acid 2,3,4,5,6-pentakis-(3-butoxy-propionyloxy)-cyclohexyl ester (136475-83-7)

Conditions	Yield
With trifluoroacetic acid for 18h; Ambient temperature;

3-(butylthio)propionic acid (22002-73-9) + myo-inositol (488-59-5) → 3-Butylsulfanyl-propionic acid 2,3,4,5,6-pentakis-(3-butylsulfanyl-propionyloxy)-cyclohexyl ester (136475-85-9)

Conditions	Yield
With trifluoroacetic acid for 18h; Ambient temperature;

Upstream product

• 608-80-0 benzenehexol 
• 87-89-8 D-myo-inositol 
• 6090-97-7 (1R,2S,3R,4S,5S,6S)-6-methoxycyclohexane-1,2,3,4,5-pentol 
• 20097-56-7 Penta-O-acetyl-myo-inosose 
• 34361-60-9 1,2;4,5-Di-O-cyclohexylidene-D-chiro-inositol 
• 86992-79-2 (1S,2S)-3-Chloro-cyclohexa-3,5-diene-1,2-diol 
• 67-56-1 methanol 
• 16940-66-2 sodium tetrahydroborate 
• 130669-73-7 (1S,2R,3R,4S,5R,6S)-2,3-dihydroxy-4,5-di-O-isopropylidene-7-oxabicyclo<4.1.0>heptane 
• 132891-77-1 6-O-Camphanoyl-1,2;4,5-di-O-cyclohexylidene-D-chiro-inositol 
• 132891-77-1 6-O-Camphanoyl-1,2;4,5-di-O-cyclohexylidene-D-myo-inositol 
• 129115-29-3 6-O-Camphanoyl-1,2;4,5-di-O-cyclohexylidene-3-O-trifluoromethanesulfonyl-D-myo-inositol 
• 129094-32-2 1,2;4,5-Di-O-cyclohexylidene-3-O-trifluoromethanesulfonyl-myo-inositol 
• 34361-60-9 1,2:4,5-dicyclohexylidene-myo-inositol 

Downstream Products

• 98510-20-4 myo-Inositol orthoformate 
• 1051375-34-8 scyllo-inositol hexaniacinate 
• 488-66-4 (2R)-2r,3c,4t,5c,6t-pentahydroxy-cyclohexanone 
• 4099-90-5 myo-inositol hexabenzoate 
• 98566-49-5 1,2,3,4,5,6-all-trans-Hexakis(octanoyloxy)cyclohexane 
• 99409-67-3 Decanoic acid 2,3,4,5,6-pentakis-decanoyloxy-cyclohexyl ester 
• 88269-10-7 Hexa-O-hexanoyl-scyllo-inosit 
• 54676-40-3 deuterised scyllo inositol 
• 129090-59-1 8-Bromo-octanoic acid 2,3,4,5,6-pentakis-(8-bromo-octanoyloxy)-cyclohexyl ester 
• 136444-88-7 6-Methylsulfanyl-hexanoic acid 2,3,4,5,6-pentakis-(6-methylsulfanyl-hexanoyloxy)-cyclohexyl ester 
• 129090-58-0 7-Bromo-heptanoic acid 2,3,4,5,6-pentakis-(7-bromo-heptanoyloxy)-cyclohexyl ester 

Relevant articles and documents

Sulfonate protecting groups. Improved synthesis of scyllo-inositol and its orthoformate from myo-inositol

A convenient high yielding method for the preparation of scyllo-inositol and its orthoformate from myo-inositol, without involving chromatography is described. myo-Inositol 1,3,5-orthoformate was benzoylated to obtain 2-O-benzoyl-myo-inositol 1,3,5-orthoformate. This diol was tosylated and the benzoyl group removed by aminolysis in a one-pot procedure to obtain 4,6-di-O-tosyl-myo-inositol 1,3,5-orthoformate. Swern oxidation of the ditosylate, followed by sodium borohydride reduction and methanolysis of tosylates gave scyllo-inositol 1,3,5-orthoformate (isolated as the triacetate). Aminolysis of the acetates followed by acid hydrolysis of the orthoformate moiety with trifluoroacetic acid gave scyllo-inositol in an overall yield of 64%.

Novel substrates for kinases involved in the biosynthesis of inositol pyrophosphates and their enhancement of atpase activity of a kinase

IP6K and PPIP5K are two kinases involved in the synthesis of inositol pyrophosphates. Synthetic analogs or mimics are necessary to understand the substrate specificity of these enzymes and to find molecules that can alter inositol pyrophosphate synthesis. In this context, we synthesized four scyllo‐inositol polyphosphates—scyllo‐IP5, scyllo‐IP6, scyllo‐IP7 and Bz‐scyllo‐IP5—from myo-inositol and studied their activity as substrates for mouse IP6K1 and the catalytic domain of VIP1, the budding yeast variant of PPIP5K. We incubated these scyllo‐inositol polyphosphates with these kinases and ATP as the phosphate donor. We tracked enzyme activity by measuring the amount of radiolabeled scyllo‐inositol pyrophosphate product formed and the amount of ATP consumed. All scyllo‐inositol polyphosphates are substrates for both the kinases but they are weaker than the corresponding myo‐inositol phosphate. Our study reveals the importance of axial-hydroxyl/phosphate for IP6K1 substrate recognition. We found that all these derivatives enhance the ATPase activity of VIP1. We found very weak ligand‐induced ATPase activity for IP6K1. Benzoyl‐scyllo‐IP5 was the most potent ligand to induce IP6K1 ATPase activity despite being a weak substrate. This compound could have potential as a competitive inhibitor.

Method for Producing Scyllo-Inositol

The disclosure provides a method of producing a scyllo-inositol or a new scyllo-inositol derivative in a one-step process, from ubiquitous and inexpensive raw materials. Also provided is a scyllo-inositol derivative bonded to saccharides such as glucose and similar.

PROCESS FOR THE PREPARATION OF SCYLLO-INOSITOL

This invention pertains to a process for manufacturing scyllo-Inositol. Specifically, the current invention pertains to a process for converting myo-Inositol to scyllo-Inositol using a bioconversion process.