ethyl 4-O-<2-O-acetyl-4,6-O-benzylidene-3-O-(chloroacetyl)-β-D-galactopyranosyl>-6-O-benzyl-2-deoxy-3-O-(p-methoxybenzyl)-2-phthalimido-1-thio-β-D-glucopyranoside

Base Information

Chemical Name:ethyl 4-O-<2-O-acetyl-4,6-O-benzylidene-3-O-(chloroacetyl)-β-D-galactopyranosyl>-6-O-benzyl-2-deoxy-3-O-(p-methoxybenzyl)-2-phthalimido-1-thio-β-D-glucopyranoside
CAS No.:115152-52-8
Molecular Formula:C₄₈H₅₀ClNO₁₄S
Molecular Weight:932.442
Hs Code.:

ethyl 4-O-<2-O-acetyl-4,6-O-benzylidene-3-O-(chloroacetyl)-β-D-galactopyranosyl>-6-O-benzyl-2-deoxy-3-O-(p-methoxybenzyl)-2-phthalimido-1-thio-β-D-glucopyranoside

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Chemical Property of ethyl 4-O-<2-O-acetyl-4,6-O-benzylidene-3-O-(chloroacetyl)-β-D-galactopyranosyl>-6-O-benzyl-2-deoxy-3-O-(p-methoxybenzyl)-2-phthalimido-1-thio-β-D-glucopyranoside

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Technology Process of ethyl 4-O-<2-O-acetyl-4,6-O-benzylidene-3-O-(chloroacetyl)-β-D-galactopyranosyl>-6-O-benzyl-2-deoxy-3-O-(p-methoxybenzyl)-2-phthalimido-1-thio-β-D-glucopyranoside

There total 7 articles about ethyl 4-O-<2-O-acetyl-4,6-O-benzylidene-3-O-(chloroacetyl)-β-D-galactopyranosyl>-6-O-benzyl-2-deoxy-3-O-(p-methoxybenzyl)-2-phthalimido-1-thio-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: 74.0%

: 115152-49-3
2-O-acetyl-4,6-O-benzylidene-3-O-(chloroacetyl)-α-D-galactopyranosyl bromide

: 115152-51-7
ethyl 6-O-benzyl-2-deoxy-3-O-(p-methoxybenzyl)-2-phthalimido-1-thio-β-D-glucopyranoside

: 115152-52-8,129519-30-8
ethyl 4-O-<2-O-acetyl-4,6-O-benzylidene-3-O-(chloroacetyl)-β-D-galactopyranosyl>-6-O-benzyl-2-deoxy-3-O-(p-methoxybenzyl)-2-phthalimido-1-thio-β-D-glucopyranoside

Guidance literature:: With 2,6-di-tert-butyl-4-methylpyridine; 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; toluene;
DOI:10.1016/0008-6215(88)80046-6

Reference yield:

: 99409-33-3
ethyl 4,6-O-benzylidene-2-deoxy-2-N-phthalamido-1-thio-β-Dglucopyranoside

: 115152-52-8,129519-30-8
ethyl 4-O-<2-O-acetyl-4,6-O-benzylidene-3-O-(chloroacetyl)-β-D-galactopyranosyl>-6-O-benzyl-2-deoxy-3-O-(p-methoxybenzyl)-2-phthalimido-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 75 percent / 60 percent sodium hydride / dimethylformamide / Ambient temperature

2: 65 percent / hydrogen chloride, sodium cyanoborohydride, molecular sieves 3A / tetrahydrofuran; diethyl ether / 0.33 h / Ambient temperature

3: 74 percent / silver triflate, 2,6-di-tert-butyl-4-methylpyridine, molecular sieves 4A / toluene; CH₂Cl₂

With hydrogenchloride; 2,6-di-tert-butyl-4-methylpyridine; 3 A molecular sieve; 4 A molecular sieve; silver trifluoromethanesulfonate; sodium hydride; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/0008-6215(88)80046-6

Reference yield:

: 104992-63-4
Methyl 4,6-O-benzylidene-1-thio-β-D-galactopyranoside

: 115152-52-8,129519-30-8
ethyl 4-O-<2-O-acetyl-4,6-O-benzylidene-3-O-(chloroacetyl)-β-D-galactopyranosyl>-6-O-benzyl-2-deoxy-3-O-(p-methoxybenzyl)-2-phthalimido-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 59 percent / pyridine; CH₂Cl₂ / 1 h / 0 °C

2: 89 percent / pyridine; CH₂Cl₂ / 2 h / 0 °C

3: 1.) bromine, tetraethylammonium bromide / 1.) dichloromethane; dichloromethane, r.t., 3 h

4: 74 percent / silver triflate, 2,6-di-tert-butyl-4-methylpyridine, molecular sieves 4A / toluene; CH₂Cl₂

With 2,6-di-tert-butyl-4-methylpyridine; 4 A molecular sieve; tetraethylammonium bromide; bromine; silver trifluoromethanesulfonate; In pyridine; dichloromethane; toluene;
DOI:10.1016/0008-6215(88)80046-6