9-{(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-9H-purin-6-ylamine

Base Information

• Chemical Name: 9-{(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-9H-purin-6-ylamine
• CAS No.: 102434-69-5
• Molecular Formula: C₃₆H₄₃N₅O₄Si
• Molecular Weight: 637.854
• Mol file: 102434-69-5.mol

Synonyms:9-{(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-9H-purin-6-ylamine

Chemical Property of 9-{(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-9H-purin-6-ylamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 9-{(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-9H-purin-6-ylamine

There total 6 articles about 9-{(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-9H-purin-6-ylamine 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: 100.0%

5'-o-monomethoxytrityl-3'-o-t-butyldimethylsilyl-N-allyloxycarbonyldeoxyadenosine (102423-04-1) → 9-{(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-9H-purin-6-ylamine (102434-69-5)

Guidance literature:

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; formic acid; N-butylamine; triphenylphosphine; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at 20 - 25 ℃; for 0.0833333h;

DOI:10.1021/jo00362a052

Reference yield: 54.0%

2'-deoxy-5-O-[(4-methoxyphenyl)(diphenyl)methyl]adenosine (51600-10-3) + tert-butyldimethylsilyl chloride (18162-48-6) → 9-{(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-9H-purin-6-ylamine (102434-69-5)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 2h; Ambient temperature;

Reference yield:

(9-{(2R,4S,5R)-4-Hydroxy-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-9H-purin-6-yl)-carbamic acid allyl ester (102423-06-3) → 9-{(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-9H-purin-6-ylamine (102434-69-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / (n-C₄H₉)4NOTs / Pd(PPh₃)4 / acetonitrile / 5.5 h / electrolysis; Pt electrodes; 10 F/mol

2: 54 percent / imidazole / dimethylformamide / 2 h / Ambient temperature

With 1H-imidazole; tetrabutylammonium p-toluenesulfonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide; acetonitrile;

upstream raw materials:

5'-o-monomethoxytrityl-3'-o-t-butyldimethylsilyl-N-allyloxycarbonyldeoxyadenosine

2'-deoxy-5-O-[(4-methoxyphenyl)(diphenyl)methyl]adenosine

tert-butyldimethylsilyl chloride

(9-{(2R,4S,5R)-4-Hydroxy-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-9H-purin-6-yl)-carbamic acid allyl ester

Downstream raw materials:

2'-deoxy-5-O-[(4-methoxyphenyl)(diphenyl)methyl]adenosine

(9-{(2R,4S,5R)-4-Hydroxy-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-9H-purin-6-yl)-carbamic acid allyl ester

5'-o-monomethoxytrityl-3'-o-t-butyldimethylsilyl-N-allyloxycarbonyldeoxyadenosine