phenylthio 2,3-di-O-benzyl-6-(tert-butyldimethylsiloxy)-α-D-mannopyranoside

Base Information

Chemical Name:phenylthio 2,3-di-O-benzyl-6-(tert-butyldimethylsiloxy)-α-D-mannopyranoside
CAS No.:1421832-73-6
Molecular Formula:C₃₂H₄₂O₅SSi
Molecular Weight:566.834
Hs Code.:

Synonyms:phenylthio 2,3-di-O-benzyl-6-(tert-butyldimethylsiloxy)-α-D-mannopyranoside

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Chemical Property of phenylthio 2,3-di-O-benzyl-6-(tert-butyldimethylsiloxy)-α-D-mannopyranoside

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Technology Process of phenylthio 2,3-di-O-benzyl-6-(tert-butyldimethylsiloxy)-α-D-mannopyranoside

There total 3 articles about phenylthio 2,3-di-O-benzyl-6-(tert-butyldimethylsiloxy)-α-D-mannopyranoside 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%

: phenyl 6-O-(tert-butyldimethylsilyl)-2-O-benzyl-1-thio-α-D-mannopyranoside

: 100-44-7
benzyl chloride

: 1421832-73-6
phenylthio 2,3-di-O-benzyl-6-(tert-butyldimethylsiloxy)-α-D-mannopyranoside

Guidance literature:: With dibutyltin chloride; tetrabutylammomium bromide; potassium carbonate; In acetonitrile; at 80 ℃; for 24h; regioselective reaction;
DOI:10.1016/j.tetlet.2017.08.043

Reference yield: 78.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 449761-78-8
phenyl 2,3-di-O-benzyl-1-thio-α-D-mannopyranoside

: 1421832-73-6
phenylthio 2,3-di-O-benzyl-6-(tert-butyldimethylsiloxy)-α-D-mannopyranoside

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 3h; regioselective reaction; Inert atmosphere;
DOI:10.1021/jo302455d

Reference yield:

: phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-α-D-mannopyranoside

: 1421832-73-6
phenylthio 2,3-di-O-benzyl-6-(tert-butyldimethylsiloxy)-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: toluene-4-sulfonic acid / dichloromethane; methanol / 18 h / 20 °C / Inert atmosphere

2: 1H-imidazole / N,N-dimethyl-formamide / 3 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; toluene-4-sulfonic acid; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo302455d