phenyl 3,4-di-O-benzyl-2-O-(4-cyanobenzenesulfonyl)-1-thio-β-L-rhamnopyranoside

Base Information

Chemical Name:phenyl 3,4-di-O-benzyl-2-O-(4-cyanobenzenesulfonyl)-1-thio-β-L-rhamnopyranoside
CAS No.:503065-82-5
Molecular Formula:C₃₃H₃₁NO₆S₂
Molecular Weight:601.744
Hs Code.:

Synonyms:phenyl 3,4-di-O-benzyl-2-O-(4-cyanobenzenesulfonyl)-1-thio-β-L-rhamnopyranoside

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Chemical Property of phenyl 3,4-di-O-benzyl-2-O-(4-cyanobenzenesulfonyl)-1-thio-β-L-rhamnopyranoside

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Technology Process of phenyl 3,4-di-O-benzyl-2-O-(4-cyanobenzenesulfonyl)-1-thio-β-L-rhamnopyranoside

There total 9 articles about phenyl 3,4-di-O-benzyl-2-O-(4-cyanobenzenesulfonyl)-1-thio-β-L-rhamnopyranoside 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: 82.0%

: 848397-88-6
S-phenyl 3,4-di-O-benzyl-1-thio-β-L-rhamnopyranoside

: 49584-26-1
p-cyanobenzenesulfonyl chloride

: 503065-82-5
phenyl 3,4-di-O-benzyl-2-O-(4-cyanobenzenesulfonyl)-1-thio-β-L-rhamnopyranoside

Guidance literature:: With triethylamine; In dichloromethane; at 20 ℃; for 36h;
DOI:10.1021/ol0340890

Reference yield:

: 100-39-0
benzyl bromide

: 503065-82-5
phenyl 3,4-di-O-benzyl-2-O-(4-cyanobenzenesulfonyl)-1-thio-β-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: 87 percent / NaH / tetrahydrofuran / Heating

2.1: 90 percent / CF₃COOH / methanol / 8 h / Heating

3.1: Bu₂SnO / benzene / 3 h / Heating

3.2: 71 percent / CsF / dimethylformamide / 18 h / 20 °C

4.1: 82 percent / Et₃N / CH₂Cl₂ / 36 h / 20 °C

With sodium hydride; di(n-butyl)tin oxide; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; benzene;
DOI:10.1021/ol0340890

Reference yield:

: 108-98-5
thiophenol

: 503065-82-5
phenyl 3,4-di-O-benzyl-2-O-(4-cyanobenzenesulfonyl)-1-thio-β-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1.1: 78 percent / NaH / hexamethylphosphoric acid triamide / 1 h / 0 °C

2.1: 95 percent / NaOMe / methanol / 3 h / 20 °C

3.1: 79 percent / CSA / acetone / 12 h / 20 °C

4.1: 87 percent / NaH / tetrahydrofuran / Heating

5.1: 90 percent / CF₃COOH / methanol / 8 h / Heating

6.1: Bu₂SnO / benzene / 3 h / Heating

6.2: 71 percent / CsF / dimethylformamide / 18 h / 20 °C

7.1: 82 percent / Et₃N / CH₂Cl₂ / 36 h / 20 °C

With camphor-10-sulfonic acid; sodium methylate; sodium hydride; di(n-butyl)tin oxide; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; acetone; benzene;
DOI:10.1021/ol0340890