ethyl 3,4-O-isopropylidene-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-1-thio-β-L-fucopyranoside

Base Information

• Chemical Name: ethyl 3,4-O-isopropylidene-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-1-thio-β-L-fucopyranoside
• CAS No.: 852311-89-8
• Molecular Formula: C₃₈H₄₈O₈S
• Molecular Weight: 664.86
• Mol file: 852311-89-8.mol

Synonyms:ethyl 3,4-O-isopropylidene-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-1-thio-β-L-fucopyranoside

Chemical Property of ethyl 3,4-O-isopropylidene-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-1-thio-β-L-fucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 3,4-O-isopropylidene-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-1-thio-β-L-fucopyranoside

There total 2 articles about ethyl 3,4-O-isopropylidene-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-1-thio-β-L-fucopyranoside 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:

perbenzyl fucosyl bromide (33639-77-9) + ethyl 3,4-di-O-isopropylidene-1-thio-β-L-fucopyranoside (138343-54-1) → ethyl 3,4-O-isopropylidene-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-1-thio-β-L-fucopyranoside (852311-89-8)

Guidance literature:

With 3 A molecular sieve; tetrabutylammomium bromide; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1016/j.bmc.2005.02.009

Reference yield:

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) → ethyl 3,4-O-isopropylidene-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-1-thio-β-L-fucopyranoside (852311-89-8)

Guidance literature:

Multi-step reaction with 2 steps

1: bromine / CH₂Cl₂ / 0.17 h / 0 °C

2: 178 mg / tetrabutylammonium bromide; molecular sieves 3 Angstroem / CH₂Cl₂; dimethylformamide / 20 °C

With 3 A molecular sieve; tetrabutylammomium bromide; bromine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2005.02.009

Reference yield: 36.0%

ethyl 3,4-O-isopropylidene-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-1-thio-β-L-fucopyranoside (852311-89-8) + 6-[N-(benzyloxycarbonylamino)hexyl]-2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(3,4-O-isopropylidene-α-L-fucopyranosyl)-β-D-glucopyranoside (852311-80-9) → 6-[N-(benzyloxycarbonylamino)hexyl]-2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-{3,4-O-isopropylidene-2-O-[3,4-O-isopropylidene-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-α-L-fucopyranosyl]-α-L-fucopyranosyl}-β-D-glucopyranoside (852311-86-5) + 6-[N-(benzyloxycarbonylamino)hexyl]-2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-{3,4-O-isopropylidene-2-O-[3,4-O-isopropylidene-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-L-fucopyranosyl]-α-L-fucopyranosyl}-β-D-glucopyranoside

Guidance literature:

With 4 A molecular sieve; tetrabutylammomium bromide; copper(ll) bromide; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; for 120h;

DOI:10.1016/j.bmc.2005.02.009

upstream raw materials:

perbenzyl fucosyl bromide

ethyl 3,4-di-O-isopropylidene-1-thio-β-L-fucopyranoside

ethyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside

Downstream raw materials:

6-[N-(benzyloxycarbonylamino)hexyl]-2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-{3,4-O-isopropylidene-2-O-[3,4-O-isopropylidene-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-α-L-fucopyranosyl]-α-L-fucopyranosyl}-β-D-glucopyranoside