phenyl 2-O-acetyl-3,4-bis-O-tert-butyldimethylsilyl-6-O-diphenylvinylsilyl-1-seleno-β-D-glucopyranoside

Base Information

• Chemical Name: phenyl 2-O-acetyl-3,4-bis-O-tert-butyldimethylsilyl-6-O-diphenylvinylsilyl-1-seleno-β-D-glucopyranoside
• CAS No.: 866417-26-7
• Molecular Formula: C₄₀H₅₈O₆SeSi₃
• Molecular Weight: 798.113

Synonyms:phenyl 2-O-acetyl-3,4-bis-O-tert-butyldimethylsilyl-6-O-diphenylvinylsilyl-1-seleno-β-D-glucopyranoside

Chemical Property of phenyl 2-O-acetyl-3,4-bis-O-tert-butyldimethylsilyl-6-O-diphenylvinylsilyl-1-seleno-β-D-glucopyranoside

Chemical Property:

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Technology Process of phenyl 2-O-acetyl-3,4-bis-O-tert-butyldimethylsilyl-6-O-diphenylvinylsilyl-1-seleno-β-D-glucopyranoside

There total 2 articles about phenyl 2-O-acetyl-3,4-bis-O-tert-butyldimethylsilyl-6-O-diphenylvinylsilyl-1-seleno-β-D-glucopyranoside 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: 83.0%

phenyl 2-O-acetyl-3,4-bis-O-tert-butyldimethylsilyl-1-seleno-β-D-glucopyranoside (866417-31-4) + vinyldiphenylchlorosilane (18419-53-9) → phenyl 2-O-acetyl-3,4-bis-O-tert-butyldimethylsilyl-6-O-diphenylvinylsilyl-1-seleno-β-D-glucopyranoside (866417-26-7)

Guidance literature:

With dmap; triethylamine; In toluene; at 20 ℃;

DOI:10.1016/j.tetlet.2005.07.087

Reference yield:

phenyl 3,4-bis-O-tert-butyldimethylsilyl-6-O-trityl-1-seleno-β-D-glucose (288584-99-6) → phenyl 2-O-acetyl-3,4-bis-O-tert-butyldimethylsilyl-6-O-diphenylvinylsilyl-1-seleno-β-D-glucopyranoside (866417-26-7)

Guidance literature:

Multi-step reaction with 3 steps

1: DMAP / acetonitrile / 12 h / 20 °C

2: 1.0 g / aq. TFA / CHCl₃ / 1 h / 20 °C

3: 83 percent / Et₃N; DMAP / toluene / 0.5 h / 20 °C

With dmap; triethylamine; trifluoroacetic acid; In chloroform; toluene; acetonitrile;

DOI:10.1021/jm051039n

Reference yield: 40.0%

phenyl 2-O-acetyl-3,4-bis-O-tert-butyldimethylsilyl-6-O-diphenylvinylsilyl-1-seleno-β-D-glucopyranoside (866417-26-7) → Acetic acid (1R,7S,8S,9R,10R)-9,10-bis-(tert-butyl-dimethyl-silanyloxy)-4,4-diphenyl-3,11-dioxa-4-sila-bicyclo[5.3.1]undec-8-yl ester (866417-32-5)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; at 80 ℃;

DOI:10.1016/j.tetlet.2005.07.087

upstream raw materials:

phenyl 2-O-acetyl-3,4-bis-O-tert-butyldimethylsilyl-1-seleno-β-D-glucopyranoside

vinyldiphenylchlorosilane

phenyl 3,4-bis-O-tert-butyldimethylsilyl-6-O-trityl-1-seleno-β-D-glucose

Downstream raw materials:

Acetic acid (1R,7S,8S,9R,10R)-9,10-bis-(tert-butyl-dimethyl-silanyloxy)-4,4-diphenyl-3,11-dioxa-4-sila-bicyclo[5.3.1]undec-8-yl ester

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