O-(2,3-di-O-benzyl-4,6-O-benzylidene-D-galactopyranosyl) trichloroacetimidate

Base Information

• Chemical Name: O-(2,3-di-O-benzyl-4,6-O-benzylidene-D-galactopyranosyl) trichloroacetimidate
• CAS No.: 1201598-10-8
• Molecular Formula: C₂₉H₂₈Cl₃NO₆
• Molecular Weight: 592.903
• Mol file: 1201598-10-8.mol

Synonyms:O-(2,3-di-O-benzyl-4,6-O-benzylidene-D-galactopyranosyl) trichloroacetimidate

Chemical Property of O-(2,3-di-O-benzyl-4,6-O-benzylidene-D-galactopyranosyl) trichloroacetimidate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of O-(2,3-di-O-benzyl-4,6-O-benzylidene-D-galactopyranosyl) trichloroacetimidate

There total 2 articles about O-(2,3-di-O-benzyl-4,6-O-benzylidene-D-galactopyranosyl) 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:

2,3-Bis-O-(phenylmethyl)-4,6-O-(phenylmethylene)-D-galactopyranose (168037-64-7) + trichloroacetonitrile (545-06-2) → O-(2,3-di-O-benzyl-4,6-O-benzylidene-D-galactopyranosyl) trichloroacetimidate (1201598-10-8)

Guidance literature:

With caesium carbonate; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1016/j.carres.2010.05.003

Reference yield:

phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside (87470-72-2) → O-(2,3-di-O-benzyl-4,6-O-benzylidene-D-galactopyranosyl) trichloroacetimidate (1201598-10-8)

Guidance literature:

Multi-step reaction with 2 steps

1: N-Bromosuccinimide / water; tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

2: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1 h / 0 °C / Inert atmosphere

With N-Bromosuccinimide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/acs.joc.1c02409

Reference yield: 74.0%

O-(2,3-di-O-benzyl-4,6-O-benzylidene-D-galactopyranosyl) trichloroacetimidate (1201598-10-8) + (2S,3S,4S)-2-azido-3,4-di-O-benzyl-octadecan-1,3,4-triol (202812-10-0) → 2-azido-3,4-di-O-benzyl-1-O-(2,3-di-O-benzyloxyl-4,6-O-benzyllidene-α-D-galactopyranosyl)-D-ribooctadecane-1,3,4-triol (951767-71-8)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -40 ℃; for 2h; Molecular sieve;

DOI:10.1016/j.bmc.2010.11.061

upstream raw materials:

2,3-Bis-O-(phenylmethyl)-4,6-O-(phenylmethylene)-D-galactopyranose

trichloroacetonitrile

phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside

Downstream raw materials:

(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1->6)-O-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl)-(1->6)-O-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

(2S,3R,4R)-3-benzyloxy-2-tert-butyldimethylsilyloxy-4-methoxyoctadecyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside

(2S,3R,4R)-3-benzyloxy-2-tert-butyldimethylsilyloxy-4-methoxyoctadecyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranoside