p-tolyl 2,3-di-O-benzyl-5-O-tert-butyldimethylsilyl-1-thio-α-D-arabinofuranoside

Base Information

Chemical Name:p-tolyl 2,3-di-O-benzyl-5-O-tert-butyldimethylsilyl-1-thio-α-D-arabinofuranoside
CAS No.:1236193-27-3
Molecular Formula:C₃₂H₄₂O₄SSi
Molecular Weight:550.835
Hs Code.:

Synonyms:p-tolyl 2,3-di-O-benzyl-5-O-tert-butyldimethylsilyl-1-thio-α-D-arabinofuranoside

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Chemical Property of p-tolyl 2,3-di-O-benzyl-5-O-tert-butyldimethylsilyl-1-thio-α-D-arabinofuranoside

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Technology Process of p-tolyl 2,3-di-O-benzyl-5-O-tert-butyldimethylsilyl-1-thio-α-D-arabinofuranoside

There total 3 articles about p-tolyl 2,3-di-O-benzyl-5-O-tert-butyldimethylsilyl-1-thio-α-D-arabinofuranoside 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: 75.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 920281-46-5
2,3-di-O-benzyl-1-(p-tolylthio)-1-deoxy-α-D-arabinofuranoside

: 1236193-27-3
p-tolyl 2,3-di-O-benzyl-5-O-tert-butyldimethylsilyl-1-thio-α-D-arabinofuranoside

Guidance literature:: With 1H-imidazole; dmap; In dichloromethane; at 20 ℃; for 2h; Inert atmosphere;
DOI:10.1021/jo100575a

Reference yield: 74.0%

: p-tolyl-2,3-di-O-acetyl-5-O-tert-butydimethylsilyl-1-thio-α-D-arabinofuranoside

: 100-39-0
benzyl bromide

: 1236193-27-3
p-tolyl 2,3-di-O-benzyl-5-O-tert-butyldimethylsilyl-1-thio-α-D-arabinofuranoside

Guidance literature:: p-tolyl-2,3-di-O-acetyl-5-O-tert-butydimethylsilyl-1-thio-α-D-arabinofuranoside; With sodium methylate; In methanol; at 20 ℃; for 3h; pH=10;

With sodium hydride; In N,N-dimethyl-formamide; kerosene; at 0 - 20 ℃; for 0.5h;

benzyl bromide; In N,N-dimethyl-formamide; kerosene; at 0 - 20 ℃; for 0.666667h;
DOI:10.1021/acs.joc.5b01686

Reference yield:

: 106-45-6
para-thiocresol

: 1236193-27-3
p-tolyl 2,3-di-O-benzyl-5-O-tert-butyldimethylsilyl-1-thio-α-D-arabinofuranoside

Guidance literature:: Multi-step reaction with 2 steps

1.1: tin(IV) chloride / dichloromethane / 0.5 h / 0 - 20 °C

2.1: sodium methylate / methanol / 3 h / 20 °C / pH 10

2.2: 0.5 h / 0 - 20 °C

2.3: 0.67 h / 0 - 20 °C

With sodium methylate; tin(IV) chloride; In methanol; dichloromethane;
DOI:10.1021/acs.joc.5b01686