methyl 4-S-(2,3-anhydro-4,6-di-O-acetyl-α-D-allopyranosyl)-2,3-di-O-p-methoxybenzyl-6-deoxy-α-D-glucopyranoside

Base Information

Chemical Name:methyl 4-S-(2,3-anhydro-4,6-di-O-acetyl-α-D-allopyranosyl)-2,3-di-O-p-methoxybenzyl-6-deoxy-α-D-glucopyranoside
CAS No.:1404060-78-1
Molecular Formula:C₃₃H₄₂O₁₂S
Molecular Weight:662.755
Hs Code.:

Synonyms:methyl 4-S-(2,3-anhydro-4,6-di-O-acetyl-α-D-allopyranosyl)-2,3-di-O-p-methoxybenzyl-6-deoxy-α-D-glucopyranoside

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Chemical Property of methyl 4-S-(2,3-anhydro-4,6-di-O-acetyl-α-D-allopyranosyl)-2,3-di-O-p-methoxybenzyl-6-deoxy-α-D-glucopyranoside

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Technology Process of methyl 4-S-(2,3-anhydro-4,6-di-O-acetyl-α-D-allopyranosyl)-2,3-di-O-p-methoxybenzyl-6-deoxy-α-D-glucopyranoside

There total 8 articles about methyl 4-S-(2,3-anhydro-4,6-di-O-acetyl-α-D-allopyranosyl)-2,3-di-O-p-methoxybenzyl-6-deoxy-α-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: 81.0%

: 1404060-76-9
methyl 2,3-di-O-p-methoxybenzyl-6-deoxy-4-thio-α-D-glucopyranoside

: 1404060-77-0
p-tolyl 2,3-anhydro-4,6-di-O-acetyl-1-thio-β-D-allopyranoside

: 1404060-78-1
methyl 4-S-(2,3-anhydro-4,6-di-O-acetyl-α-D-allopyranosyl)-2,3-di-O-p-methoxybenzyl-6-deoxy-α-D-glucopyranoside

Guidance literature:: p-tolyl 2,3-anhydro-4,6-di-O-acetyl-1-thio-β-D-allopyranoside; With trifluoromethylsulfonic anhydride; phosphorus pentoxide; 1,1'-sulfinylbisbenzene; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; at -78 ℃; for 0.5h; Molecular sieve;

methyl 2,3-di-O-p-methoxybenzyl-6-deoxy-4-thio-α-D-glucopyranoside; In dichloromethane; at -78 ℃; for 2h;
DOI:10.1016/j.tet.2012.09.037

Reference yield:

: 1404060-73-6
methyl 2,3-di-O-p-methoxybenzyl-6-deoxy-4-iodo-α-D-galactopyranoside

: 1404060-78-1
methyl 4-S-(2,3-anhydro-4,6-di-O-acetyl-α-D-allopyranosyl)-2,3-di-O-p-methoxybenzyl-6-deoxy-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: N,N-dimethyl-formamide / 2 h / 20 - 90 °C

2.1: potassium carbonate / methanol / 12 h / 20 °C

2.2: acidic resin / pH 7

3.1: trifluoromethylsulfonic anhydride; phosphorus pentoxide; 1,1'-sulfinylbisbenzene; 2,4,6-tri-tert-butylpyrimidine / dichloromethane / 0.5 h / -78 °C / Molecular sieve

3.2: 2 h / -78 °C

With trifluoromethylsulfonic anhydride; phosphorus pentoxide; 1,1'-sulfinylbisbenzene; potassium carbonate; 2,4,6-tri-tert-butylpyrimidine; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2012.09.037

Reference yield:

: 1404060-74-7
methyl 2,3-di-O-p-methoxybenzyl-4-acetylthio-6-deoxy-α-D-glucopyranoside

: 1404060-78-1
methyl 4-S-(2,3-anhydro-4,6-di-O-acetyl-α-D-allopyranosyl)-2,3-di-O-p-methoxybenzyl-6-deoxy-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1.1: potassium carbonate / methanol / 12 h / 20 °C

1.2: acidic resin / pH 7

2.1: trifluoromethylsulfonic anhydride; phosphorus pentoxide; 1,1'-sulfinylbisbenzene; 2,4,6-tri-tert-butylpyrimidine / dichloromethane / 0.5 h / -78 °C / Molecular sieve

2.2: 2 h / -78 °C

With trifluoromethylsulfonic anhydride; phosphorus pentoxide; 1,1'-sulfinylbisbenzene; potassium carbonate; 2,4,6-tri-tert-butylpyrimidine; In methanol; dichloromethane;
DOI:10.1016/j.tet.2012.09.037