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

Base Information

• Chemical Name: phenyl 3,4-bis-O-tert-butyldimethylsilyl-6-O-trityl-1-seleno-β-D-glucose
• CAS No.: 288584-99-6
• Molecular Formula: C₄₃H₅₈O₅SeSi₂
• Molecular Weight: 790.062
• Mol file: 288584-99-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about phenyl 3,4-bis-O-tert-butyldimethylsilyl-6-O-trityl-1-seleno-β-D-glucose 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: 66.0%

Benzeneselenol (645-96-5) + (2R,3R,4R)-3,4-bis(tert-butyldimethylsiloxy)-3,4-dihydro-2-(triphenylmethoxymethyl)-2H-pyran (288584-98-5) → phenyl 3,4-bis-O-tert-butyldimethylsilyl-6-O-trityl-1-seleno-β-D-glucose (288584-99-6)

Guidance literature:

(2R,3R,4R)-3,4-bis(tert-butyldimethylsiloxy)-3,4-dihydro-2-(triphenylmethoxymethyl)-2H-pyran; With 3,3-dimethyldioxirane; In dichloromethane;

Benzeneselenol; With triethylamine; In dichloromethane;

DOI:10.1016/S0040-4039(00)00556-6

Reference yield:

1,5-anhydro-2-deoxy-6-O-trityl-D-arabino-hex-1-enitol (122350-80-5) → phenyl 3,4-bis-O-tert-butyldimethylsilyl-6-O-trityl-1-seleno-β-D-glucose (288584-99-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 85 percent / imidazole / dimethylformamide / 12 h / 60 °C

2.1: dimethyldioxirane / CH₂Cl₂; acetone / 0 - 20 °C

2.2: Et₃N / CH₂Cl₂ / 1.75 h / -20 °C

With 1H-imidazole; 3,3-dimethyldioxirane; In dichloromethane; N,N-dimethyl-formamide; acetone; 1.1: Condensation / 2.1: Oxidation / 2.2: Addition;

DOI:10.1021/jo0002339

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → phenyl 3,4-bis-O-tert-butyldimethylsilyl-6-O-trityl-1-seleno-β-D-glucose (288584-99-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 85 percent / imidazole / dimethylformamide / 12 h / 60 °C

2.1: dimethyldioxirane / CH₂Cl₂; acetone / 0 - 20 °C

2.2: Et₃N / CH₂Cl₂ / 1.75 h / -20 °C

With 1H-imidazole; 3,3-dimethyldioxirane; In dichloromethane; N,N-dimethyl-formamide; acetone; 1.1: Condensation / 2.1: Oxidation / 2.2: Addition;

DOI:10.1021/jo0002339

upstream raw materials:

Benzeneselenol

(2R,3R,4R)-3,4-bis(tert-butyldimethylsiloxy)-3,4-dihydro-2-(triphenylmethoxymethyl)-2H-pyran

1,5-anhydro-2-deoxy-6-O-trityl-D-arabino-hex-1-enitol

tert-butyldimethylsilyl chloride

Downstream raw materials:

phenyl 2-O-(allyl(dimethyl)silyl)-3,4-bis-O-(tert-butyl(dimethyl)silyl)-6-O-(triphenylmethyl)-1-seleno-β-D-glucopyranoside

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

Acetic acid (2S,3R,4R,5R,6R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-phenylselanyl-6-trityloxymethyl-tetrahydro-pyran-3-yl ester

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