2-O-(4-methoxybenzyl)-3,4,6-tri-O-acetyl-α-D-galactopyranosyl-(1,3)-2-O-benzoyl-3-thio-3-deoxy-4,6-O-benzylidene-β-D-galactopyranosyl-(1,4)-2,3,6-tri-O-benzoyl-α-D-glucopyranosyl-trichloroacetimide

Base Information

Chemical Name:2-O-(4-methoxybenzyl)-3,4,6-tri-O-acetyl-α-D-galactopyranosyl-(1,3)-2-O-benzoyl-3-thio-3-deoxy-4,6-O-benzylidene-β-D-galactopyranosyl-(1,4)-2,3,6-tri-O-benzoyl-α-D-glucopyranosyl-trichloroacetimide
CAS No.:914097-82-8
Molecular Formula:C₆₉H₆₆Cl₃NO₂₃S
Molecular Weight:1415.7
Hs Code.:

2-O-(4-methoxybenzyl)-3,4,6-tri-O-acetyl-α-D-galactopyranosyl-(1,3)-2-O-benzoyl-3-thio-3-deoxy-4,6-O-benzylidene-β-D-galactopyranosyl-(1,4)-2,3,6-tri-O-benzoyl-α-D-glucopyranosyl-trichloroacetimide

Synonyms:2-O-(4-methoxybenzyl)-3,4,6-tri-O-acetyl-α-D-galactopyranosyl-(1,3)-2-O-benzoyl-3-thio-3-deoxy-4,6-O-benzylidene-β-D-galactopyranosyl-(1,4)-2,3,6-tri-O-benzoyl-α-D-glucopyranosyl-trichloroacetimide

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Chemical Property of 2-O-(4-methoxybenzyl)-3,4,6-tri-O-acetyl-α-D-galactopyranosyl-(1,3)-2-O-benzoyl-3-thio-3-deoxy-4,6-O-benzylidene-β-D-galactopyranosyl-(1,4)-2,3,6-tri-O-benzoyl-α-D-glucopyranosyl-trichloroacetimide

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Technology Process of 2-O-(4-methoxybenzyl)-3,4,6-tri-O-acetyl-α-D-galactopyranosyl-(1,3)-2-O-benzoyl-3-thio-3-deoxy-4,6-O-benzylidene-β-D-galactopyranosyl-(1,4)-2,3,6-tri-O-benzoyl-α-D-glucopyranosyl-trichloroacetimide

There total 17 articles about 2-O-(4-methoxybenzyl)-3,4,6-tri-O-acetyl-α-D-galactopyranosyl-(1,3)-2-O-benzoyl-3-thio-3-deoxy-4,6-O-benzylidene-β-D-galactopyranosyl-(1,4)-2,3,6-tri-O-benzoyl-α-D-glucopyranosyl-trichloroacetimide 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: 70.0%

: 914097-79-3
allyl 2-O-(4-methoxybenzyl)-3,4,6-tri-O-acetyl-α-D-galactopyranosyl-(1,3)-2-O-benzoyl-3-thio-3-deoxy-4,6-O-benzylidene-β-D-galactopyranosyl-(1,4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside

: 545-06-2
trichloroacetonitrile

: 914097-82-8
2-O-(4-methoxybenzyl)-3,4,6-tri-O-acetyl-α-D-galactopyranosyl-(1,3)-2-O-benzoyl-3-thio-3-deoxy-4,6-O-benzylidene-β-D-galactopyranosyl-(1,4)-2,3,6-tri-O-benzoyl-α-D-glucopyranosyl-trichloroacetimide

Guidance literature:: allyl 2-O-(4-methoxybenzyl)-3,4,6-tri-O-acetyl-α-D-galactopyranosyl-(1,3)-2-O-benzoyl-3-thio-3-deoxy-4,6-O-benzylidene-β-D-galactopyranosyl-(1,4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside; With triethylsilane; tetrakis(triphenylphosphine) palladium⁽⁰⁾; zinc(II) chloride; In tetrahydrofuran;

trichloroacetonitrile; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1021/ol062199b

Reference yield:

: (2R,3R,4S,5R,6R)-6-Allyloxy-2-hydroxymethyl-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-3,4-diol

: 914097-82-8
2-O-(4-methoxybenzyl)-3,4,6-tri-O-acetyl-α-D-galactopyranosyl-(1,3)-2-O-benzoyl-3-thio-3-deoxy-4,6-O-benzylidene-β-D-galactopyranosyl-(1,4)-2,3,6-tri-O-benzoyl-α-D-glucopyranosyl-trichloroacetimide

Guidance literature:: Multi-step reaction with 4 steps

1.1: 1.60 g / pyridine / 20 °C

2.1: ZnCl₂; Pd(PPh₃)4; Et₃SiH / tetrahydrofuran

2.2: 0.61 g / DBU / CH₂Cl₂ / 2 h / 20 °C

3.1: 165 mg / molecular sieves; TMSOTf / CH₂Cl₂ / 1.25 h / -20 - 20 °C

4.1: ZnCl₂; Pd(PPh₃)4; Et₃SiH / tetrahydrofuran

4.2: 70 percent / DBU / CH₂Cl₂ / 2 h / 20 °C

With pyridine; triethylsilane; tetrakis(triphenylphosphine) palladium⁽⁰⁾; molecular sieve; trimethylsilyl trifluoromethanesulfonate; zinc(II) chloride; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol062199b

Reference yield:

: 914097-72-6
allyl 2-O-(4-methoxybenzyl)-3,4-O-isopropylidene-6-O-(1-methoxy-1-methylethyl)-β-D-galactopyranoside

: 914097-82-8
2-O-(4-methoxybenzyl)-3,4,6-tri-O-acetyl-α-D-galactopyranosyl-(1,3)-2-O-benzoyl-3-thio-3-deoxy-4,6-O-benzylidene-β-D-galactopyranosyl-(1,4)-2,3,6-tri-O-benzoyl-α-D-glucopyranosyl-trichloroacetimide

Guidance literature:: Multi-step reaction with 5 steps

1.1: p-TsOH / methanol

2.1: 1.60 g / pyridine / 20 °C

3.1: ZnCl₂; Pd(PPh₃)4; Et₃SiH / tetrahydrofuran

3.2: 0.61 g / DBU / CH₂Cl₂ / 2 h / 20 °C

4.1: 165 mg / molecular sieves; TMSOTf / CH₂Cl₂ / 1.25 h / -20 - 20 °C

5.1: ZnCl₂; Pd(PPh₃)4; Et₃SiH / tetrahydrofuran

5.2: 70 percent / DBU / CH₂Cl₂ / 2 h / 20 °C

With pyridine; triethylsilane; tetrakis(triphenylphosphine) palladium⁽⁰⁾; molecular sieve; trimethylsilyl trifluoromethanesulfonate; toluene-4-sulfonic acid; zinc(II) chloride; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/ol062199b