methyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl-α-(1->4)-2,3-O-isopropylidene-1-α-L-rhamnopyranoside

Base Information

Chemical Name:methyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl-α-(1->4)-2,3-O-isopropylidene-1-α-L-rhamnopyranoside
CAS No.:1380218-15-4
Molecular Formula:C₃₇H₄₅N₃O₉
Molecular Weight:675.779
Hs Code.:

Synonyms:methyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl-α-(1->4)-2,3-O-isopropylidene-1-α-L-rhamnopyranoside

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Chemical Property of methyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl-α-(1->4)-2,3-O-isopropylidene-1-α-L-rhamnopyranoside

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Technology Process of methyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl-α-(1->4)-2,3-O-isopropylidene-1-α-L-rhamnopyranoside

There total 3 articles about methyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl-α-(1->4)-2,3-O-isopropylidene-1-α-L-rhamnopyranoside 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: 84.0%

: 14133-63-2
methyl 2,3-O-isopropylidene-α-L-rhamnoside

: 4′-methylphenyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-1-thio-β-D-glucoside

: 1380218-15-4
methyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl-α-(1->4)-2,3-O-isopropylidene-1-α-L-rhamnopyranoside

Guidance literature:: 4′-methylphenyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-1-thio-β-D-glucoside; With 4-morpholinecarboxaldehyde; In dichloromethane; for 0.333333h; Molecular sieve;

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -10 ℃;

methyl 2,3-O-isopropylidene-α-L-rhamnoside; In dichloromethane; at -10 ℃; for 12h;
DOI:10.1021/ol402519c

Reference yield:

: 14133-63-2
methyl 2,3-O-isopropylidene-α-L-rhamnoside

: 4′-methylphenyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-1-thio-β-D-glucoside

: 1380218-16-5
methyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl-β-(1->4)-2,3-O-isopropylidene-1-α-L-rhamnopyranoside

: 1380218-15-4
methyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl-α-(1->4)-2,3-O-isopropylidene-1-α-L-rhamnopyranoside

Guidance literature:: methyl 2,3-O-isopropylidene-α-L-rhamnoside; 4′-methylphenyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-1-thio-β-D-glucoside; In dichloromethane; acetonitrile; for 0.5h; Molecular sieve; Inert atmosphere;

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; acetonitrile; at -60 ℃; for 1.5h; Overall yield = 60 %; Overall yield = 93 mg; Inert atmosphere;
DOI:10.1021/ol402519c

Reference yield:

: 4-methylphenyl 2-azido-2-deoxy-1-thio-α,β-D-glucopyranoside

: 1380218-16-5
methyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl-β-(1->4)-2,3-O-isopropylidene-1-α-L-rhamnopyranoside

: 1380218-15-4
methyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl-α-(1->4)-2,3-O-isopropylidene-1-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: sodium hydride / N,N-dimethyl-formamide / 2 h / 0 - 20 °C / Inert atmosphere

2: dichloromethane

With sodium hydride; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.201200173