O-(3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-N-carbobenzyloxy-L-threonine methyl ester

Base Information

Chemical Name:O-(3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-N-carbobenzyloxy-L-threonine methyl ester
CAS No.:1423497-16-8
Molecular Formula:C₄₀H₄₅NO₉
Molecular Weight:683.799
Hs Code.:

Synonyms:O-(3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-N-carbobenzyloxy-L-threonine methyl ester

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Chemical Property of O-(3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-N-carbobenzyloxy-L-threonine methyl ester

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Technology Process of O-(3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-N-carbobenzyloxy-L-threonine methyl ester

There total 6 articles about O-(3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-N-carbobenzyloxy-L-threonine methyl ester 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: 86.0%

: p-methylphenyl 3,4,6-tri-O-benzyl-2-deoxy-1-thio-D-glucopyranoside

: 57224-63-2
methyl (2S,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutyrate

: 1423497-13-5
O-(3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-N-carbobenzyloxy-L-threonine methyl ester

: 1423497-16-8
O-(3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-N-carbobenzyloxy-L-threonine methyl ester

Guidance literature:: p-methylphenyl 3,4,6-tri-O-benzyl-2-deoxy-1-thio-D-glucopyranoside; With silver trifluoromethanesulfonate; p-toluenesulfonyl chloride; In dichloromethane; at -78 ℃; for 0.25h; Inert atmosphere; Molecular sieve;

methyl (2S,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutyrate; In dichloromethane; at -78 ℃; Overall yield = 92 %; diastereoselective reaction; Inert atmosphere; Molecular sieve;
DOI:10.1002/chem.201203418

Reference yield:

: 55628-54-1
3,4,6-tri-O-benzyl-D-glucal

: 57224-63-2
methyl (2S,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutyrate

: 1423497-13-5
O-(3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-N-carbobenzyloxy-L-threonine methyl ester

: 1423497-16-8
O-(3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-N-carbobenzyloxy-L-threonine methyl ester

Guidance literature:: With trimethylsilyl bromide; Triphenylphosphine oxide; In dichloromethane; at 20 ℃; under 760.051 Torr; Overall yield = 74 %; diastereoselective reaction; Inert atmosphere;
DOI:10.3762/bjoc.12.164

Reference yield:

: 57224-63-2
methyl (2S,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutyrate

: 1360560-44-6
p-methylphenyl 3,4,6-tri-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside

: 1423497-13-5
O-(3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-N-carbobenzyloxy-L-threonine methyl ester

: 1423497-16-8
O-(3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-N-carbobenzyloxy-L-threonine methyl ester

Guidance literature:: p-methylphenyl 3,4,6-tri-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside; With N-iodo-succinimide; In dichloromethane; at -40 ℃; for 1h; Inert atmosphere;

With trifluorormethanesulfonic acid; In dichloromethane; at -40 ℃; for 0.5h; Inert atmosphere;

methyl (2S,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutyrate; In dichloromethane; at -40 ℃; for 3h; Overall yield = 94 percent; diastereoselective reaction; Inert atmosphere;
DOI:10.1002/anie.201906297