2,3-di-O-acetyl-4,6-O-benzylidene-D-glucopyranosyl trichloroacetimidate

Base Information

• Chemical Name: 2,3-di-O-acetyl-4,6-O-benzylidene-D-glucopyranosyl trichloroacetimidate
• CAS No.: 206866-61-7
• Molecular Formula: C₁₉H₂₀Cl₃NO₈
• Molecular Weight: 496.729
• Mol file: 206866-61-7.mol

Synonyms:2,3-di-O-acetyl-4,6-O-benzylidene-D-glucopyranosyl trichloroacetimidate

Chemical Property of 2,3-di-O-acetyl-4,6-O-benzylidene-D-glucopyranosyl trichloroacetimidate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3-di-O-acetyl-4,6-O-benzylidene-D-glucopyranosyl trichloroacetimidate

There total 3 articles about 2,3-di-O-acetyl-4,6-O-benzylidene-D-glucopyranosyl trichloroacetimidate 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: 76.0%

2,3-di-O-acetyl-4,6-O-benzylidene-D-glucopyranose (22893-78-3,104186-84-7,108031-63-6,113566-71-5,113566-72-6) + trichloroacetonitrile (545-06-2) → 2,3-di-O-acetyl-4,6-O-benzylidene-D-glucopyranosyl trichloroacetimidate (206866-61-7)

Guidance literature:

With caesium carbonate; In dichloromethane;

DOI:10.1021/ja991361l

Reference yield:

4,6-O-benzylidene-D-glucose (3006-41-5,20771-09-9,25152-90-3,97232-16-1,104022-77-7,113566-67-9,113566-68-0) → 2,3-di-O-acetyl-4,6-O-benzylidene-D-glucopyranosyl trichloroacetimidate (206866-61-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / DMAP; pyridine / 0 - 20 °C

2: 78 percent / benzylamine / tetrahydrofuran / 0 - 20 °C

3: 76 percent / Cs₂CO₃ / CH₂Cl₂

With pyridine; dmap; caesium carbonate; benzylamine; In tetrahydrofuran; dichloromethane; 1: Acetylation / 2: Deacetylation / 3: acetimidation;

DOI:10.1021/ja991361l

Reference yield:

acetyl 2,3-di-O-acetyl-4,6-O-benzyliden-D-glucopyranoside (180980-45-4) → 2,3-di-O-acetyl-4,6-O-benzylidene-D-glucopyranosyl trichloroacetimidate (206866-61-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / benzylamine / tetrahydrofuran / 0 - 20 °C

2: 76 percent / Cs₂CO₃ / CH₂Cl₂

With caesium carbonate; benzylamine; In tetrahydrofuran; dichloromethane; 1: Deacetylation / 2: acetimidation;

DOI:10.1021/ja991361l

upstream raw materials:

2,3-di-O-acetyl-4,6-O-benzylidene-D-glucopyranose

trichloroacetonitrile

4,6-O-benzylidene-D-glucose

acetyl 2,3-di-O-acetyl-4,6-O-benzyliden-D-glucopyranoside

Downstream raw materials:

ethyl 4,6-O-benzylidene-β-D-glucopyranosyl-(1→3)-2-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside