p-methylphenyl 2-O-benzoyl-4,6-di-O-benzyl-3-O-tert-butyldimethylsilyl-1-thio-β-D-galactoside

Base Information

Chemical Name:p-methylphenyl 2-O-benzoyl-4,6-di-O-benzyl-3-O-tert-butyldimethylsilyl-1-thio-β-D-galactoside
CAS No.:1269466-90-1
Molecular Formula:C₄₀H₄₈O₆SSi
Molecular Weight:684.969
Hs Code.:

Synonyms:p-methylphenyl 2-O-benzoyl-4,6-di-O-benzyl-3-O-tert-butyldimethylsilyl-1-thio-β-D-galactoside

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Chemical Property of p-methylphenyl 2-O-benzoyl-4,6-di-O-benzyl-3-O-tert-butyldimethylsilyl-1-thio-β-D-galactoside

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Technology Process of p-methylphenyl 2-O-benzoyl-4,6-di-O-benzyl-3-O-tert-butyldimethylsilyl-1-thio-β-D-galactoside

There total 10 articles about p-methylphenyl 2-O-benzoyl-4,6-di-O-benzyl-3-O-tert-butyldimethylsilyl-1-thio-β-D-galactoside 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: 91.0%

: 1269466-85-4
p-tolyl 2-O-benzoyl-3-O-tert-butyldimethylsilyl-4-O-benzyl-1-thio-β-D-galactopyranosidede

: 100-39-0
benzyl bromide

: 1269466-90-1
p-methylphenyl 2-O-benzoyl-4,6-di-O-benzyl-3-O-tert-butyldimethylsilyl-1-thio-β-D-galactoside

Guidance literature:: With sodium hydride; In dichloromethane; N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃; for 3h;
DOI:10.1021/ol200192d

Reference yield:

: p-methylphenyl 2-O-benzoyl-3,4-O-benzylidene-1-thio-β-D-galactopyranoside

: 1269466-90-1
p-methylphenyl 2-O-benzoyl-4,6-di-O-benzyl-3-O-tert-butyldimethylsilyl-1-thio-β-D-galactoside

Guidance literature:: Multi-step reaction with 4 steps

1: camphor-10-sulfonic acid / acetonitrile / 8 h / 20 °C

2: 1H-imidazole / dichloromethane / 3 h / 20 °C / Inert atmosphere

3: borane-THF; trimethylsilyl trifluoromethanesulfonate / tetrahydrofuran; dichloromethane / 5 h / 0 °C / Inert atmosphere

4: sodium hydride / dichloromethane; N,N-dimethyl-formamide; mineral oil / 3 h / 0 - 20 °C

With 1H-imidazole; borane-THF; trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; sodium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile; mineral oil; 4: Williamson synthesis;
DOI:10.1021/ol200192d

Reference yield:

: 1269466-82-1
p-methylphenyl 2-O-benzoyl-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-1-thio-β-D-galactoside

: 1269466-90-1
p-methylphenyl 2-O-benzoyl-4,6-di-O-benzyl-3-O-tert-butyldimethylsilyl-1-thio-β-D-galactoside

Guidance literature:: Multi-step reaction with 2 steps

1: borane-THF; trimethylsilyl trifluoromethanesulfonate / tetrahydrofuran; dichloromethane / 5 h / 0 °C / Inert atmosphere

2: sodium hydride / dichloromethane; N,N-dimethyl-formamide; mineral oil / 3 h / 0 - 20 °C

With borane-THF; trimethylsilyl trifluoromethanesulfonate; sodium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; mineral oil; 2: Williamson synthesis;
DOI:10.1021/ol200192d