4-methylphenyl 2,3-di-O-acetyl-4-azido-6-O-benzoyl-4-deoxy-1-thio-β-D-galactopyranoside

Base Information

Chemical Name:4-methylphenyl 2,3-di-O-acetyl-4-azido-6-O-benzoyl-4-deoxy-1-thio-β-D-galactopyranoside
CAS No.:849834-74-8
Molecular Formula:C₂₄H₂₅N₃O₇S
Molecular Weight:499.544
Hs Code.:

Synonyms:4-methylphenyl 2,3-di-O-acetyl-4-azido-6-O-benzoyl-4-deoxy-1-thio-β-D-galactopyranoside

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Chemical Property of 4-methylphenyl 2,3-di-O-acetyl-4-azido-6-O-benzoyl-4-deoxy-1-thio-β-D-galactopyranoside

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Technology Process of 4-methylphenyl 2,3-di-O-acetyl-4-azido-6-O-benzoyl-4-deoxy-1-thio-β-D-galactopyranoside

There total 1 articles about 4-methylphenyl 2,3-di-O-acetyl-4-azido-6-O-benzoyl-4-deoxy-1-thio-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: 86.0%

: 849834-73-7
(2S,3R,4S,5R)-5-hydroxy-6-(hydroxymethyl)-2-(p-tolylthio)tetrahydro-2H-pyran-3,4-diyldiacetate

: 98-88-4
benzoyl chloride

: 849834-74-8
4-methylphenyl 2,3-di-O-acetyl-4-azido-6-O-benzoyl-4-deoxy-1-thio-β-D-galactopyranoside

Guidance literature:: (2S,3R,4S,5R)-5-hydroxy-6-(hydroxymethyl)-2-(p-tolylthio)tetrahydro-2H-pyran-3,4-diyldiacetate; benzoyl chloride; With pyridine; In dichloromethane; at -78 - 20 ℃;

With trifluoromethanesulfonic acid anhydride; In dichloromethane; at -78 - 20 ℃;

With sodium azide; In N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2005.01.015

Reference yield: 93.0%

: 849834-74-8
4-methylphenyl 2,3-di-O-acetyl-4-azido-6-O-benzoyl-4-deoxy-1-thio-β-D-galactopyranoside

: 98-88-4
benzoyl chloride

: 849834-75-9
4-methylphenyl 4-azido-2,3,6-tri-O-benzoyl-4-deoxy-1-thio-β-D-galactopyranoside

Guidance literature:: 4-methylphenyl 2,3-di-O-acetyl-4-azido-6-O-benzoyl-4-deoxy-1-thio-β-D-galactopyranoside; With sodium methylate; In methanol; for 5h;

benzoyl chloride; With pyridine; dmap;
DOI:10.1016/j.tet.2005.01.015

Reference yield:

: 849834-74-8
4-methylphenyl 2,3-di-O-acetyl-4-azido-6-O-benzoyl-4-deoxy-1-thio-β-D-galactopyranoside

: 849834-76-0
2-bromoethyl 4-azido-2,3,6-tri-O-benzoyl-4-deoxy-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1.1: NaOMe / methanol / 5 h

1.2: 93 percent / pyridine; DMAP

2.1: 89 percent / MS AW-300; N-iodosuccinimide; trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 0.17 h / 0 °C

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; MS AW-300; sodium methylate; In methanol; dichloromethane;
DOI:10.1016/j.tet.2005.01.015