methyl 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-6-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-2-deoxy-β-D-glucopyranoside

Base Information

Chemical Name:methyl 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-6-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-2-deoxy-β-D-glucopyranoside
CAS No.:97242-83-6
Molecular Formula:C₅₀H₆₄N₂O₁₈
Molecular Weight:981.061
Hs Code.:

methyl 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-6-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-2-deoxy-β-D-glucopyranoside

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Chemical Property of methyl 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-6-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-2-deoxy-β-D-glucopyranoside

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Technology Process of methyl 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-6-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-2-deoxy-β-D-glucopyranoside

There total 9 articles about methyl 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-6-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-2-deoxy-β-D-glucopyranoside 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: 65.0%

: 33639-77-9
perbenzyl fucosyl bromide

: 97242-82-5
methyl 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-2-deoxy-β-D-glucopyranoside

: 97242-83-6
methyl 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-6-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-2-deoxy-β-D-glucopyranoside

Guidance literature:: With molecular sieve; tetraethylammonium bromide; In dichloromethane; N,N-dimethyl-formamide; for 16h; Ambient temperature;
DOI:10.1139/v85-182

Reference yield:

: 76101-14-9
methyl-2-desoxy-2-phthalimido-β-D-glucopyranoside

: 97242-83-6
methyl 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-6-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-2-deoxy-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: 85 percent / p-toluenesulphonic acid / acetonitrile

2: 86 percent / sodium hydride / 1,2-dimethoxy-ethane

3: 95 percent / molecular sieves, sodium cyanoborohydride, HCl / tetrahydrofuran; diethyl ether / 1 h / Ambient temperature

4: 46 percent / collidine, silver triflate / nitromethane / 1.) -25 deg C, 4 h; 2.) rt, overnight

5: 1.) hydrazine hydrate / 1.) 95percent aqueous ethanol, reflux, 30 min; 2.) pyridine, rt, overnight

6: 87 percent / hydrogen / palladium-on-carbon / methanol / 16 h

7: 65 percent / tetraethylammonium bromide, molecular sieves / CH₂Cl₂; dimethylformamide / 16 h / Ambient temperature

With 2,3,5-trimethyl-pyridine; hydrogenchloride; molecular sieve; tetraethylammonium bromide; hydrogen; silver trifluoromethanesulfonate; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; hydrazine hydrate; palladium on activated charcoal; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; nitromethane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1139/v85-182

Reference yield:

: 97242-79-0
methyl 3,6-di-O-benzyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside

: 97242-83-6
methyl 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-6-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-2-deoxy-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 46 percent / collidine, silver triflate / nitromethane / 1.) -25 deg C, 4 h; 2.) rt, overnight

2: 1.) hydrazine hydrate / 1.) 95percent aqueous ethanol, reflux, 30 min; 2.) pyridine, rt, overnight

3: 87 percent / hydrogen / palladium-on-carbon / methanol / 16 h

4: 65 percent / tetraethylammonium bromide, molecular sieves / CH₂Cl₂; dimethylformamide / 16 h / Ambient temperature

With 2,3,5-trimethyl-pyridine; molecular sieve; tetraethylammonium bromide; hydrogen; silver trifluoromethanesulfonate; hydrazine hydrate; palladium on activated charcoal; In methanol; nitromethane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1139/v85-182