2,3,4-tri-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-α-D-glucopyranosyl trichloroacetimidate

Base Information

• Chemical Name: 2,3,4-tri-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-α-D-glucopyranosyl trichloroacetimidate
• CAS No.: 866719-69-9
• Molecular Formula: C₄₅H₄₂Cl₃NO₉Si
• Molecular Weight: 875.274
• Mol file: 866719-69-9.mol

Synonyms:2,3,4-tri-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-α-D-glucopyranosyl trichloroacetimidate

Chemical Property of 2,3,4-tri-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-α-D-glucopyranosyl trichloroacetimidate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3,4-tri-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-α-D-glucopyranosyl trichloroacetimidate

There total 7 articles about 2,3,4-tri-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-α-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: 94.0%

trichloroacetonitrile (545-06-2) + 2,3,4-tri-O-benzoyl-6-O-[tert-butyl(diphenyl)silyl]-D-glucopyranose → 2,3,4-tri-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-α-D-glucopyranosyl trichloroacetimidate (866719-69-9)

Guidance literature:

With caesium carbonate; In dichloromethane; at 0 - 20 ℃; for 3h;

DOI:10.1021/acs.orglett.9b03038

Reference yield:

trichloroacetonitrile (545-06-2) + phenyl 2,3,4-tri-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-1-thio-α-D-glucopyranoside (1029696-25-0) → 2,3,4-tri-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-α-D-glucopyranosyl trichloroacetimidate (866719-69-9)

Guidance literature:

phenyl 2,3,4-tri-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-1-thio-α-D-glucopyranoside; With N-Bromosuccinimide; water; In acetone; at 25 ℃; for 2h;

trichloroacetonitrile; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 25 ℃; for 16h; Further stages.;

DOI:10.1039/b717446b

Reference yield:

benzoyl chloride (98-88-4) → 2,3,4-tri-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-α-D-glucopyranosyl trichloroacetimidate (866719-69-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: dmap; pyridine / 5 h / 0 - 20 °C / Inert atmosphere

1.2: 0 °C / Inert atmosphere

2.1: hydrazinium monoacetate / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

3.1: caesium carbonate / dichloromethane / 3 h / 0 - 20 °C

With pyridine; dmap; hydrazinium monoacetate; caesium carbonate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/acs.orglett.9b03038

upstream raw materials:

trichloroacetonitrile

phenyl 2,3,4-tri-O-benzoyl-6-O-(t-butyldiphenylsilyl)-1-thio-β-D-glucopyranoside

phenyl 2,3,4-tri-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-1-thio-α-D-glucopyranoside

benzoyl chloride

Downstream raw materials:

methyl O-[O-(2,3,4-tri-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-β-D-glucopyranosyl)-(1->6)-(2,3,4-tri-O-benzoyl-β-D-glucopyranosyl)]-(1->6)-(2,3,4-tri-O-octadecanoyl-α-D-glucopyranoside

methyl O-{O-[O-(2,3,4-tri-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-β-D-glucopyranosyl)-(1->6)-(2,3,4-tri-O-benzoyl-β-D-glucopyranosyl)]-(1->6)-(2,3,4-tri-O-benzoyl-β-D-glucopyranosyl)}-(1->6)-2,3,4-tri-O-octadecanoyl-α-D-glucopyranoside

methyl O-(2,3,4-tri-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-octadecanoyl-α-D-glucopyranoside

pent-4-enyl 2,3,4-tri-O-benzoyl-β-D-glucopyranoside