(E)-3-[(2R,3S,5R)-5-(6-Benzoylamino-purin-9-yl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-acrylic acid ethyl ester

Base Information

• Chemical Name: (E)-3-[(2R,3S,5R)-5-(6-Benzoylamino-purin-9-yl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-acrylic acid ethyl ester
• CAS No.: 156100-68-4
• Molecular Formula: C₂₇H₃₅N₅O₅Si
• Molecular Weight: 537.691
• Mol file: 156100-68-4.mol

Synonyms:

Chemical Property of (E)-3-[(2R,3S,5R)-5-(6-Benzoylamino-purin-9-yl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-acrylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-3-[(2R,3S,5R)-5-(6-Benzoylamino-purin-9-yl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-acrylic acid ethyl ester

There total 2 articles about (E)-3-[(2R,3S,5R)-5-(6-Benzoylamino-purin-9-yl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-acrylic acid ethyl ester 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:

5’-O-(4,4’dimethoxytrityl)-N6-(benzoyl)-3’-O-tert-butyldimethylsilyldeoxyadenosine (146578-12-3) → (E)-3-[(2R,3S,5R)-5-(6-Benzoylamino-purin-9-yl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-acrylic acid ethyl ester (156100-68-4)

Guidance literature:

Multi-step reaction with 3 steps

1: ZnBr₂ / nitromethane / 6 h / 0 °C

2: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) -78 deg C, 2.) -78 deg C

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; zinc dibromide; In nitromethane;

DOI:10.1016/S0040-4039(00)61716-1

Reference yield:

5'-aldehyde-2'-deoxy-6-N-benzoyl-3'-O-tertbutyldimethylsilyl adenosine (167700-45-0) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → (E)-3-[(2R,3S,5R)-5-(6-Benzoylamino-purin-9-yl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-acrylic acid ethyl ester (156100-68-4)

Guidance literature:

Yield given;

DOI:10.1016/S0040-4039(00)61716-1

Reference yield:

(E)-3-[(2R,3S,5R)-5-(6-Benzoylamino-purin-9-yl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-acrylic acid ethyl ester (156100-68-4) → C56H66N8O9Si

Guidance literature:

Multi-step reaction with 3 steps

1: H₂ / Pd-C

2: i-Bu₂AlH / -78 °C

3: NaCNBH₃ / aq. ethanol / pH 5,5

With hydrogen; diisobutylaluminium hydride; sodium cyanoborohydride; palladium on activated charcoal; In ethanol;

DOI:10.1016/S0040-4039(00)61716-1

upstream raw materials:

5'-aldehyde-2'-deoxy-6-N-benzoyl-3'-O-tertbutyldimethylsilyl adenosine

ethyl (triphenylphosphoranylidene)acetate

5’-O-(4,4’dimethoxytrityl)-N6-(benzoyl)-3’-O-tert-butyldimethylsilyldeoxyadenosine

Downstream raw materials:

N-{9-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(3-oxo-propyl)-tetrahydro-furan-2-yl]-9H-purin-6-yl}-benzamide