3-O-Benzyl-1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose

Base Information

• Chemical Name: 3-O-Benzyl-1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose
• CAS No.: 18685-18-2
• Molecular Formula: C19H26 O6
• Molecular Weight: 350.412
• Hs Code.: 2940000080
• NSC Number: 56267
• Mol file: 18685-18-2.mol

Synonyms:18685-18-2;3-O-Benzyl-1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose;5-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole;1,2:5,6-Bis-O-(1-methylethylidene)-3-O-(phenylmethyl)-alpha-D-glucofuranose;BRN 0043822;NSC 56267;NSC56267;alpha-D-Glucofuranose, 1,2:5,6-bis-O-(1-methylethylidene)-3-O-(phenylmethyl)-;SCHEMBL2312455;NSC-56267;AKOS030254888;(3aR,5R)-6-[(Benzyl-4-D)oxy]-5-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole;PS-11003;SY246335;FT-0662747;FT-0772251;A900895;3-0-benzyl-1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose;3-O-Benzyl-1,2,5,6-di-O-isopropylidene-alpha-D-glucofuranose;3-O-Benzyl 1,2:5,6,-di-O-isopropylidene-alpha-D-glucofuranose;.alpha.D-Galactofuranose, 1,2:5,6-bis-O-(1-methylethylidene)-3-O-(phenylmethyl)-;3-O-Benzyl-1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose(3aR,5R,6S,6aR)-6-(benzyloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole;6-Benzyloxy-5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

Chemical Property of 3-O-Benzyl-1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose

Chemical Property:

• Appearance/Colour: Colourless syrup
• Vapor Pressure: 5.85E-07mmHg at 25°C
• Melting Point: 60-65ºC
• Refractive Index: 1.4925
• Boiling Point: 422.6 °C at 760 mmHg
• Flash Point: 168.3 °C
• PSA: 55.38000
• Density: 1.21 g/cm³
• LogP: 2.59970
• Storage Temp.: Refrigerator
• Solubility.: Soluble in chloroform
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 350.17293854
• Heavy Atom Count: 25
• Complexity: 473

Purity/Quality:

98%, ^*data from raw suppliers

3-O-Benzyl-1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OCC(O1)C2C(C3C(O2)OC(O3)(C)C)OCC4=CC=CC=C4)C
• Uses: A derivative of glucofuranose.

Technology Process of 3-O-Benzyl-1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose

There total 25 articles about 3-O-Benzyl-1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose 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: 100.0%

benzyl bromide (100-39-0) + 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5) → 3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose (18685-18-2)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; at 20 ℃; for 5h;

DOI:10.1016/S0008-6215(02)00085-X

Reference yield: 98.0%

benzyl chloride (100-44-7) + 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5) → 3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose (18685-18-2)

Guidance literature:

With sodium hydride; In tetrahydrofuran; for 24h; Ambient temperature;

DOI:10.1016/S0040-4039(00)92630-3

Reference yield: 97.0%

3-O-acetyl-1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose (16713-80-7) + benzyl bromide (100-39-0) → 3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose (18685-18-2)

Guidance literature:

With sodium hydroxide; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1016/j.carres.2005.03.007

upstream raw materials:

benzyl bromide

Natrium-Verbindung der O¹,O²;O⁵,O⁶-Diisopropyliden-α-D-glucofuranose

benzyl chloride

D-Glucose

Downstream raw materials:

3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose

1,2,4,6-tetra-O-acetyl-3-O-benzyl-β-D-glucopyranose

3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose diacetate

2-azido-2-(6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-yl)ethanol

Refernces

• 1、 Czernecki et al.. "-". . p. 3535. Retrieved 1976.
• 2、 Karakawa, Makoto,Nakatsubo, Fumiaki. "An improved method for the preparation of 3-O-benzyl-6-O-pivaloyl-α-D-glucopyranose 1,2,4-orthopivalate". . p. 951 - 954. Retrieved 2002.
• 3、 Benedekovi?, Goran,Popsavin, Mirjana,Radulovi?, Niko S.,Stojanovi?-Radi?, Zorica,Farkas, Sándor,Francuz, Jovana,Popsavin, Velimir. "Synthesis and antimicrobial activity of (?)-cleistenolide and analogues". supporting information. . Retrieved 2020/12/07.
• 4、 -. "Gram-level total synthesis method of sulfur onium salt type natural product neoponkoranol extracted from salacia plants". Paragraph 0029; 0030; 0031; 0032. . Retrieved 2019/02/19.