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

Base Information

• Chemical Name: 5'-o-monomethoxytrityl-3'-o-t-butyldimethylsilyl-N-allyloxycarbonyldeoxyadenosine
• CAS No.: 102423-04-1
• Molecular Formula: C₄₀H₄₇N₅O₆Si
• Molecular Weight: 721.929
• Mol file: 102423-04-1.mol

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

Chemical Property of 5'-o-monomethoxytrityl-3'-o-t-butyldimethylsilyl-N-allyloxycarbonyldeoxyadenosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5'-o-monomethoxytrityl-3'-o-t-butyldimethylsilyl-N-allyloxycarbonyldeoxyadenosine

There total 7 articles about 5'-o-monomethoxytrityl-3'-o-t-butyldimethylsilyl-N-allyloxycarbonyldeoxyadenosine 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: 95.0%

allyl 1-benzotriazolyl carbonate (102423-16-5) + Carbonic acid allyl ester (2R,3S,5R)-2-hydroxymethyl-5-[4-(4-methoxy-benzoylamino)-2-oxo-3,4-dihydro-2H-pyrimidin-1-yl]-tetrahydro-furan-3-yl ester → 5'-o-monomethoxytrityl-3'-o-t-butyldimethylsilyl-N-allyloxycarbonyldeoxyadenosine (102423-04-1)

Guidance literature:

With tert.-butyl lithium; In tetrahydrofuran; at -78 ℃; for 0.0833333h;

DOI:10.1021/jo00362a052

Reference yield: 95.0%

allyl 1-benzotriazolyl carbonate (102423-16-5) + 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) → 5'-o-monomethoxytrityl-3'-o-t-butyldimethylsilyl-N-allyloxycarbonyldeoxyadenosine (102423-04-1)

Guidance literature:

With tert.-butyl lithium; In tetrahydrofuran; hexane; pentane; at -78 ℃; for 0.166667h;

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) → 5'-o-monomethoxytrityl-3'-o-t-butyldimethylsilyl-N-allyloxycarbonyldeoxyadenosine (102423-04-1)

Guidance literature:

Multi-step reaction with 3 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

3: 95 percent / t-BuLi / tetrahydrofuran; pentane; hexane / 0.17 h / -78 °C

With 1H-imidazole; tert.-butyl lithium; tetrabutylammonium p-toluenesulfonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; acetonitrile; pentane;

upstream raw materials:

allyl 1-benzotriazolyl carbonate

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

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

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

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