1,3,4,6-Tetra-O-acetyl-2-deoxy-D-glucopyranose

Base Information

• Chemical Name: 1,3,4,6-Tetra-O-acetyl-2-deoxy-D-glucopyranose
• CAS No.: 69515-91-9
• Molecular Formula: C14H20O9
• Molecular Weight: 332.307
• DSSTox Substance ID: DTXSID50447840
• Nikkaji Number: J928.524E
• Mol file: 69515-91-9.mol

Synonyms:1,3,4,6-Tetra-O-acetyl-2-deoxy-D-glucopyranose;69515-91-9;[(2R,3S,4R)-3,4,6-triacetyloxyoxan-2-yl]methyl acetate;2-DEOXY-D-GLUCOSE-TETRAACETATE;SCHEMBL5792080;DTXSID50447840;AKOS030240810;AS-81974;2-Deoxy-D-arabino-hexopyranose tetraacetate;1,3,4,6-tetra-O-acetyl-2-desoxy-d-glucopyranose;W-203547;[(2R,3S,4R)-3,4,6-TRIS(ACETYLOXY)OXAN-2-YL]METHYL ACETATE

Chemical Property of 1,3,4,6-Tetra-O-acetyl-2-deoxy-D-glucopyranose

Chemical Property:

• Melting Point: 70-74°C
• PSA: 114.43000
• LogP: 0.09100
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 9
• Exact Mass: 332.11073221
• Heavy Atom Count: 23
• Complexity: 473

Purity/Quality:

98% ^*data from raw suppliers

1,3,4,6-Tetra-O-acetyl-2-deoxy-D-glucopyranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(CC(O1)OC(=O)C)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H](CC(O1)OC(=O)C)OC(=O)C)OC(=O)C
• Uses: 2-Deoxy-D-glucose Tetraacetate (cas# 69515-91-9) is a compound useful in organic synthesis.

Technology Process of 1,3,4,6-Tetra-O-acetyl-2-deoxy-D-glucopyranose

There total 14 articles about 1,3,4,6-Tetra-O-acetyl-2-deoxy-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: 95.0%

acetic acid (64-19-7,77671-22-8) + D-glucal triacetate (2873-29-2) → 1,3,4,6-tetra-O-acetyl-2-deoxy-D-glucopyranose (69515-91-9)

Guidance literature:

With hydrogen bromide; acetic anhydride; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/ol035705v

Reference yield: 89.9%

2-deoxy-D-arabino-hexopyranose (61-58-5,13299-15-5,13299-16-6,14215-77-1,14215-78-2,20789-85-9,23568-30-1,25494-04-6,34339-39-4,34339-40-7,34339-46-3,34339-47-4,114717-20-3,114717-21-4,137491-75-9,137491-76-0) + acetic anhydride (108-24-7) → 1,3,4,6-tetra-O-acetyl-2-deoxy-D-glucopyranose (69515-91-9)

Guidance literature:

With pyridine; at 25 ℃; for 16h;

DOI:10.3390/ijms20030697

Reference yield: 86.0%

methyl 3,4,6-tri-O-acetyl-2-deoxy-α/β-D-glucopyranoside (126873-07-2) → 1,3,4,6-tetra-O-acetyl-2-deoxy-D-glucopyranose (69515-91-9)

Guidance literature:

With acetic anhydride; sulfuric acid; In acetic acid; at 0 - 20 ℃; for 2h;

upstream raw materials:

D-glucal triacetate

2-deoxy-D-arabino-hexopyranose

acetic anhydride

acetic acid

Downstream raw materials:

S-phenyl 3,4,6-tri-O-acetyl-2-deoxy-β-D-arabino-thiohexopyranoside

thiophenyl 2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranoside

p-nitrophenyl 2-deoxy-α-D-arabino-hexopyranoside

C₄₁H₄₆O₁₂