1,2-anhydro-alpha-D-glucopyranose 3,4,6-triacetate

Base Information

• Chemical Name: 1,2-anhydro-alpha-D-glucopyranose 3,4,6-triacetate
• CAS No.: 3867-86-5
• Molecular Formula: C₁₂H₁₆O₈
• Molecular Weight: 288.254
• Mol file: 3867-86-5.mol

Synonyms:Glucopyranose,1,2-anhydro-, triacetate, a-D- (6CI,7CI,8CI); a-D-Glucopyranose, 1,2-anhydro-, triacetate (9CI); 2,7-Dioxabicyclo[4.1.0]heptane,a-D-glucopyranoside deriv.;1,2-Anhydro-a-D-glucopyranose3,4,6-triacetate; 3,4,6-Tri-O-acetyl-1,2-anhydro-a-D-glucopyranose; Brigl's anhydride

Chemical Property of 1,2-anhydro-alpha-D-glucopyranose 3,4,6-triacetate

Chemical Property:

• PSA: 100.66000
• LogP: -0.46340

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1,2-anhydro-alpha-D-glucopyranose 3,4,6-triacetate

There total 7 articles about 1,2-anhydro-alpha-D-glucopyranose 3,4,6-triacetate 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: 67.0%

D-glucal triacetate (2873-29-2) → Brigl's anhydride (3867-86-5,5624-44-2) + 3,4,6-tri-O-acetyl-1,2-anhydro-β-D-mannopyranose (161016-87-1)

Guidance literature:

With 2,6-dichloropyridine N-oxide; poly(ethylene glycol)-attached ruthenium porphyrim; In dichloromethane; at 40 ℃; for 24h;

DOI:10.1021/ol0259138

Reference yield:

D-glucal triacetate (2873-29-2) → Brigl's anhydride (3867-86-5,5624-44-2)

Guidance literature:

With 2,6-dichloropyridine N-oxide; ruthenium porphyrins on a styrene-divinylbenzene copolymer; In benzene; at 40 ℃; for 48h;

DOI:10.1021/ja000461k

Reference yield:

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → Brigl's anhydride (3867-86-5,5624-44-2)

Guidance literature:

Multi-step reaction with 2 steps

1: ammonium chloride; zinc / acetonitrile / 0.5 h / 60 °C

2: sodium hydrogencarbonate; Oxone / dichloromethane; acetone; water / 0.5 h / 0 °C

With Oxone; sodium hydrogencarbonate; ammonium chloride; zinc; In dichloromethane; water; acetone; acetonitrile;

upstream raw materials:

3,4,6-tri-O-acetyl-β-D-glucopyranosyl chloride

2-O-trichloroacetyl-3,4,6-tri-O-acetyl-β-D-glucopyranosyl chloride

D-glucal triacetate

tetrachloromethane

Downstream raw materials:

2,3,4-tri-O-acetyllevoglucosan

benzyl 3,4,6-tri-O-acetyl-β-D-glucopyranoside

tert-butyl-(tetra-O-acetyl-β-D-glucopyranoside)

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