2-Deoxy-L-ribose

Base Information

• Chemical Name: 2-Deoxy-L-ribose
• CAS No.: 18546-37-7
• Molecular Formula: C5H10O4
• Molecular Weight: 134.132
• Hs Code.: 29329990
• DSSTox Substance ID: DTXSID50939972
• Nikkaji Number: J859.473B
• Wikipedia: L-Deoxyribose
• Wikidata: Q6456094
• Mol file: 18546-37-7.mol

Synonyms:2-DEOXY-L-RIBOSE;18546-37-7;(3R,4S)-3,4,5-trihydroxypentanal;2-deoxy-L-erythro-pentose;L-erythro-Pentose, 2-deoxy-;L-erythro-Pentose,2-deoxy-;desoxyribose;D-2-Deoxyribose;EINECS 208-573-0;MFCD09880214;BRN 1721978;AI3-52228;SCHEMBL574324;CHEBI:27816;DTXSID50939972;ASJSAQIRZKANQN-UHNVWZDZSA-N;AKOS006282569;AKOS015855817;AM83958;GS-3353;(3R,4S)-3,4,5-tris(oxidanyl)pentanal;2-Deoxy-L-ribose, >=97.0% (TLC);A812964;Q6456094

Chemical Property of 2-Deoxy-L-ribose

Chemical Property:

• Appearance/Colour: white to light beige crystalline powder
• Vapor Pressure: 2.53E-07mmHg at 25°C
• Melting Point: 69-72 °C
• Refractive Index: 1.5
• Boiling Point: 332.1 °C at 760 mmHg
• PKA: 13.58±0.20(Predicted)
• Flash Point: 154.6 °C
• PSA: 69.92000
• Density: 1.516 g/cm³
• LogP: -1.55310
• Storage Temp.: 2-8°C
• Solubility.: Methanol (Slightly), Water (Slightly)
• XLogP3: -2.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 134.05790880
• Heavy Atom Count: 9
• Complexity: 83

Purity/Quality:

99% ^*data from raw suppliers

2-Deoxy-L-ribose ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 24/25-37/39-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Nucleic Acids and Derivatives
• Canonical SMILES: C(C=O)C(C(CO)O)O
• Isomeric SMILES: C(C=O)[C@H]([C@H](CO)O)O
• Uses: 2-Deoxy-L-ribose is an isomer of 2-Deoxy-D-ribose (D252000) which induces apoptosis by inhibiting the synthesis and increasing the efflux of glutathione.

Technology Process of 2-Deoxy-L-ribose

There total 14 articles about 2-Deoxy-L-ribose which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

N'-[(2R,4R)-4-Allyl-2-phenyl-[1,3]dioxan-(5E)-ylidene]-N,N-dimethyl-hydrazine → 2-deoxy-D-ribose (533-67-5,1724-14-7,5284-18-4,18546-36-6,18546-37-7,40156-57-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 88 percent / ammonium dihydrogen phosphate / tetrahydrofuran; H₂O / 7 h / Ambient temperature

2: NH₃ / tetrahydrofuran; H₂O / 4 h / Ambient temperature

3: NaBH₄ / tetrahydrofuran; H₂O / 0 °C / to RT

4: 1.) O₃; 2.) Me₂S / 1.) MeOH, -78 deg C; 2.) MeOH, -78 deg C to RT, overnight

5: aq. trifluoroacetic acid

With sodium tetrahydroborate; dihydrogen phosphate ammonium salt; dimethylsulfide; ammonia; ozone; trifluoroacetic acid; In tetrahydrofuran; water;

DOI:10.3891/acta.chem.scand.51-1041

Reference yield:

(2R,4R)-4-Allyl-2-phenyl-[1,3]dioxan-5-one → 2-deoxy-D-ribose (533-67-5,1724-14-7,5284-18-4,18546-36-6,18546-37-7,40156-57-8)

Guidance literature:

Multi-step reaction with 4 steps

1: NH₃ / tetrahydrofuran; H₂O / 4 h / Ambient temperature

2: NaBH₄ / tetrahydrofuran; H₂O / 0 °C / to RT

3: 1.) O₃; 2.) Me₂S / 1.) MeOH, -78 deg C; 2.) MeOH, -78 deg C to RT, overnight

4: aq. trifluoroacetic acid

With sodium tetrahydroborate; dimethylsulfide; ammonia; ozone; trifluoroacetic acid; In tetrahydrofuran; water;

DOI:10.3891/acta.chem.scand.51-1041

Reference yield:

(2R,4S)-4-Allyl-2-phenyl-[1,3]dioxan-5-one → 2-deoxy-D-ribose (533-67-5,1724-14-7,5284-18-4,18546-36-6,18546-37-7,40156-57-8)

Guidance literature:

Multi-step reaction with 3 steps

1: NaBH₄ / tetrahydrofuran; H₂O / 0 °C / to RT

2: 1.) O₃; 2.) Me₂S / 1.) MeOH, -78 deg C; 2.) MeOH, -78 deg C to RT, overnight

3: aq. trifluoroacetic acid

With sodium tetrahydroborate; dimethylsulfide; ozone; trifluoroacetic acid; In tetrahydrofuran; water;

DOI:10.3891/acta.chem.scand.51-1041

upstream raw materials:

2-deoxy-4,5-O-isopropylidene-L-ribose ethylene acetal

5,5-dimethoxy-pent-2c-en-1-ol

5-hydroxy-pent-3-ynal-dimethylacetal

Downstream raw materials:

N-phenyl-α-DL-erythro-2-deoxy-pentopyranosylamine

(2S,3R)-2-Hydroxymethyl-5-methoxy-tetrahydro-furan-3-ol

Refernces

• 1、 Ulven, Trond,Sorbye, Karsten A.,Carlsen, Per H. J.. "Synthesis of racemic 3,5-?-benzylidene-2-deoxypentoses from 2-phenyl-1,3-dioxan-5-one hydrate". . p. 1041 - 1044. Retrieved 2007/10/03.