O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)trichloroacetimidate

Base Information

• Chemical Name: O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)trichloroacetimidate
• CAS No.: 120703-59-5
• Molecular Formula: C₂₉H₃₀Cl₃NO₅
• Molecular Weight: 578.92
• Mol file: 120703-59-5.mol

Synonyms:O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)trichloroacetimidate

Chemical Property of O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)trichloroacetimidate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)trichloroacetimidate

There total 11 articles about O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)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: 100.0%

2,3,4-tri-O-benzyl-6-deoxy-α-L-galactopyranose (33639-75-7) + trichloroacetonitrile (545-06-2) → O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)trichloroacetimidate (120703-59-5)

Guidance literature:

With caesium carbonate; In dichloromethane; at 20 ℃; for 2h; Molecular sieve;

DOI:10.1271/bbb.80609

Reference yield: 69.0%

(3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol (162118-38-9) + trichloroacetonitrile (545-06-2) → O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)trichloroacetimidate (120703-59-5)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1515/HC.2010.16.2-3.105

Reference yield: 41.0%

ethyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside (116514-50-2,128962-63-0,131545-02-3,136758-06-0,99409-34-4,116391-11-8) + trichloroacetonitrile (545-06-2) → O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)trichloroacetimidate (120703-59-5)

Guidance literature:

ethyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside; With N-Bromosuccinimide; water; In acetone; for 0.0833333h;

trichloroacetonitrile; With caesium carbonate; In dichloromethane; at 20 ℃; for 6h;

DOI:10.1002/chem.201202064

upstream raw materials:

2,3,4-tri-O-benzyl-6-deoxy-α-L-galactopyranose

trichloroacetonitrile

(3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol

6-deoxy-L-galactose

Downstream raw materials:

dibenzyl 2,3,4-tri-O-benzyl-α-L-fucopyranosyl phosphate

dibenzyl 2,3,4-tri-O-benzyl-β-L-fucopyranosyl phosphate

tert-Butyldimethylsilyl O-(2,6-Di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-<(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)>-2-azido-6-O-benzyl-2-deoxy-β-D-glucopyranoside

[(2R,4aR,6S,7R,8R,8aS)-7-Azido-2-phenyl-8-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-tert-butyl-dimethyl-silane