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

Base Information

• Chemical Name: N-{9-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(3-oxo-propyl)-tetrahydro-furan-2-yl]-9H-purin-6-yl}-benzamide
• CAS No.: 156100-65-1
• Molecular Formula: C₂₅H₃₃N₅O₄Si
• Molecular Weight: 495.654
• Mol file: 156100-65-1.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about N-{9-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(3-oxo-propyl)-tetrahydro-furan-2-yl]-9H-purin-6-yl}-benzamide 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) → N-{9-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(3-oxo-propyl)-tetrahydro-furan-2-yl]-9H-purin-6-yl}-benzamide (156100-65-1)

Guidance literature:

Multi-step reaction with 5 steps

1: ZnBr₂ / nitromethane / 6 h / 0 °C

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

4: H₂ / Pd-C

5: i-Bu₂AlH / -78 °C

With oxalyl dichloride; hydrogen; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; zinc dibromide; palladium on activated charcoal; In nitromethane;

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

Reference yield:

3-[(2R,3S,5R)-5-(6-Benzoylamino-purin-9-yl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-propionic acid ethyl ester → N-{9-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(3-oxo-propyl)-tetrahydro-furan-2-yl]-9H-purin-6-yl}-benzamide (156100-65-1)

Guidance literature:

With diisobutylaluminium hydride; at -78 ℃; Yield given;

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

Reference yield:

6-N-benzoyl-3'-O-(tert-butyldimethylsilyl)-2'-deoxyadenosine (51549-40-7) → N-{9-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(3-oxo-propyl)-tetrahydro-furan-2-yl]-9H-purin-6-yl}-benzamide (156100-65-1)

Guidance literature:

Multi-step reaction with 4 steps

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

3: H₂ / Pd-C

4: i-Bu₂AlH / -78 °C

With oxalyl dichloride; hydrogen; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; palladium on activated charcoal;

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

upstream raw materials:

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

6-N-benzoyl-3'-O-(tert-butyldimethylsilyl)-2'-deoxyadenosine

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

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