1,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranose

Base Information

• Chemical Name: 1,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranose
• CAS No.: 4692-12-0
• Molecular Formula: C14H20O10
• Molecular Weight: 348.307
• European Community (EC) Number: 610-322-9
• DSSTox Substance ID: DTXSID401281122
• Nikkaji Number: J567.978H
• Mol file: 4692-12-0.mol

Synonyms:1,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranose;4292-12-0;4692-12-0;[(2R,3R,4R,5R,6R)-3,4,6-triacetyloxy-5-hydroxyoxan-2-yl]methyl acetate;(2R,3R,4R,5R,6R)-6-(acetoxymethyl)-3-hydroxytetrahydro-2H-pyran-2,4,5-triyl triacetate;[(2R,3R,4R,5R,6R)-3,4,6-TRIS(ACETYLOXY)-5-HYDROXYOXAN-2-YL]METHYL ACETATE;.alpha.-D-Glucopyranose,1,3,4,6-tetraacetate;.alpha.-D-Glucopyranose, 1,3,4,6-tetraacetate;SCHEMBL1337942;DTXSID401281122;BS-28046;alpha-D-Glucopyranose 1,3,4,6-tetraacetate;1,3,4,6-Tetra-O-acetylalpha-D-glucopyranose;alpha-D-Glucopyranose, 1,3,4,6-tetraacetate

Chemical Property of 1,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranose

Chemical Property:

• PSA: 134.66000
• LogP: -0.93820
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 9
• Exact Mass: 348.10564683
• Heavy Atom Count: 24
• Complexity: 502

Purity/Quality:

1,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranose 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)OC(=O)C)O)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)OC(=O)C)O)OC(=O)C)OC(=O)C

Technology Process of 1,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranose

There total 9 articles about 1,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranose 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: 56.0%

ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside (32934-24-0,41670-79-5,52645-73-5,55722-49-1,79389-52-9,99031-86-4,125354-48-5,126187-25-5) → 2,3,4,5-tetra-O-acetyl-D-glucopyranose (3947-62-4,6207-76-7,19235-21-3,22554-70-7,22860-22-6,47339-09-3,57884-82-9,62057-79-8,70191-05-8,109525-54-4,140147-37-1,10343-06-3) + 1,3,4,6-tetra-O-acetyl glucopyranose (4692-12-0)

Guidance literature:

With N-Bromosuccinimide; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; water; at 0 ℃;

DOI:10.1016/j.tetlet.2003.09.230

Reference yield: 21.0%

C46H70O14 → 2,3,4,6-tetraacetylglucose (3947-62-4,10343-06-3,19235-21-3,22554-70-7,22860-22-6,47339-09-3,57884-82-9,62057-79-8,70191-05-8,109525-54-4,140147-37-1,6207-76-7) + 2-((3R,4R,5R,8R,9R,10R,13S,14R,15R)-13-Hydroxymethyl-15-isopropenyl-4-methoxycarbonylmethyl-4,9,10-trimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl)-2-methyl-propionic acid methyl ester (159258-86-3) + C46H70O14 + 1,3,4,6-tetra-O-acetyl glucopyranose (4692-12-0)

Guidance literature:

In chloroform;

DOI:10.1135/cccc19971776

Reference yield: 16.0%

phenyl 2,3,4,6-tetra-O-acetyl-1-seleno-β-D-glucopyranoside (23661-29-2,23661-30-5) + acetonitrile (75-05-8,26809-02-9) → 2,3,4,5-tetra-O-acetyl-D-glucopyranose (3947-62-4,6207-76-7,19235-21-3,22554-70-7,22860-22-6,47339-09-3,57884-82-9,62057-79-8,70191-05-8,109525-54-4,140147-37-1,10343-06-3) + N-acetyl-2,3,4,6-tetra-O-acetyl-α-D-glucopyranosylamine (6983-35-3,29399-21-1,35923-05-8,35923-06-9,35923-07-0,101399-28-4,76051-35-9) + 1,3,4,6-tetra-O-acetyl glucopyranose (4692-12-0)

Guidance literature:

With oxygen; N-methyl-1-quinolinium hexafluorophosphate; 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose; In toluene; at 20 ℃; diastereoselective reaction; Molecular sieve; UV-irradiation; Air atmosphere;

DOI:10.1080/07328303.2011.601533

upstream raw materials:

D-Glucose

acetic anhydride

α-D-glucopyranose peracetylate

methyl-alpha-D-glucopyranoside

Downstream raw materials:

1,3,4,6-tetra-O-acetyl-2-O-<2-(chloroacetoxymethyl)benzoyl>-α-D-glucopyranose

O-<3,4,6-tri-O-acetyl-2-O-<2-(chloroacetoxymethyl)benzoyl>-β-D-glucopyranosyl>-(1->2)-1,3,4,6-tetra-O-acetyl-α-D-glucopyranose

1,3,4,6-Tetra-O-acetyl-2-O-(phenylacetyl)-α-D-glucopyranose

1,3,4,6-tetra-O-acetyl-2-O-benzyl-α-D-glucopyranoside