methyl 2-azido-3-O-(2-O-benzoyl-4-O-benzyl-3,6-dideoxy-β-D-ribo-hexopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside

Base Information

Chemical Name:methyl 2-azido-3-O-(2-O-benzoyl-4-O-benzyl-3,6-dideoxy-β-D-ribo-hexopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside
CAS No.:496065-36-2
Molecular Formula:C₃₄H₃₇N₃O₉
Molecular Weight:631.682
Hs Code.:

Synonyms:methyl 2-azido-3-O-(2-O-benzoyl-4-O-benzyl-3,6-dideoxy-β-D-ribo-hexopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside

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Chemical Property of methyl 2-azido-3-O-(2-O-benzoyl-4-O-benzyl-3,6-dideoxy-β-D-ribo-hexopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside

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Technology Process of methyl 2-azido-3-O-(2-O-benzoyl-4-O-benzyl-3,6-dideoxy-β-D-ribo-hexopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside

There total 1 articles about methyl 2-azido-3-O-(2-O-benzoyl-4-O-benzyl-3,6-dideoxy-β-D-ribo-hexopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside 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: 83.0%

: 96093-11-7
Methyl-2-azido-4,6-O-benzylidene-2-desoxy-β-D-galactopyranoside

: phenyl 2-O-benzoyl-4-O-benzyl-3,6-dideoxy-1-thio-α,β-D-ribo-hexopyranoside

: 496065-36-2
methyl 2-azido-3-O-(2-O-benzoyl-4-O-benzyl-3,6-dideoxy-β-D-ribo-hexopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside

Guidance literature:: Methyl-2-azido-4,6-O-benzylidene-2-desoxy-β-D-galactopyranoside; phenyl 2-O-benzoyl-4-O-benzyl-3,6-dideoxy-1-thio-α,β-D-ribo-hexopyranoside; With N-iodo-succinimide; 4 A molecular sieve; In dichloromethane; at -60 ℃; for 1h;

With trifluorormethanesulfonic acid; In dichloromethane; at -60 - -30 ℃; for 3h;
DOI:10.1139/v02-117

Reference yield: 94.0%

: 496065-36-2
methyl 2-azido-3-O-(2-O-benzoyl-4-O-benzyl-3,6-dideoxy-β-D-ribo-hexopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside

: 496065-37-3
methyl 2-azido-3-O-(4-O-benzyl-3,6-dideoxy-β-D-ribo-hexopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside

Guidance literature:: With sodium methylate; In methanol; for 2h;
DOI:10.1139/v02-117

Reference yield:

: 496065-36-2
methyl 2-azido-3-O-(2-O-benzoyl-4-O-benzyl-3,6-dideoxy-β-D-ribo-hexopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside

: 496065-47-5
methyl 2-acetamido-3-O-(2-O-benzoyl-3,4,6-trideoxy-β-D-threo-hexopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1: 94 percent / sodium methoxide / methanol / 2 h

2: 82 percent / dimethyl sulfoxide; acetic anhydride / 20 °C

3: 92 percent / L-selectride / tetrahydrofuran / 1 h / 0 °C

4: 102 mg / tetrahydrofuran; H₂O / 0.5 h

5: 87 percent / pyridine / CH₂Cl₂

6: 78 percent / ammonium formate / 5 percent Pd/C / methanol / 1 h / Heating

7: 92 percent / toluene / 8 h / Heating

8: 83 percent / tributyltin hydride; azobis(isobutyronitrile) / toluene / 3 h / Heating

With pyridine; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium methylate; ammonium formate; acetic anhydride; L-Selectride; dimethyl sulfoxide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; toluene; 1: Zemplen transesterification / 8: Barton-McCombie deoxygenation;
DOI:10.1139/v02-117