2-amino-9-{(2R,4S,5R)-4-(tert-butyldimethylsilyloxy)-5-[(tert-butyldimethylsilyloxy)methyl]tetrahydrofuran-2-yl}-9H-purine-6-yl 2,4,6-triisopropylbenzenesulfonate

Base Information

• Chemical Name: 2-amino-9-{(2R,4S,5R)-4-(tert-butyldimethylsilyloxy)-5-[(tert-butyldimethylsilyloxy)methyl]tetrahydrofuran-2-yl}-9H-purine-6-yl 2,4,6-triisopropylbenzenesulfonate
• CAS No.: 328238-59-1
• Molecular Formula: C₃₇H₆₃N₅O₆SSi₂
• Molecular Weight: 762.174
• Mol file: 328238-59-1.mol

Synonyms:2-amino-9-{(2R,4S,5R)-4-(tert-butyldimethylsilyloxy)-5-[(tert-butyldimethylsilyloxy)methyl]tetrahydrofuran-2-yl}-9H-purine-6-yl 2,4,6-triisopropylbenzenesulfonate

Chemical Property of 2-amino-9-{(2R,4S,5R)-4-(tert-butyldimethylsilyloxy)-5-[(tert-butyldimethylsilyloxy)methyl]tetrahydrofuran-2-yl}-9H-purine-6-yl 2,4,6-triisopropylbenzenesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-amino-9-{(2R,4S,5R)-4-(tert-butyldimethylsilyloxy)-5-[(tert-butyldimethylsilyloxy)methyl]tetrahydrofuran-2-yl}-9H-purine-6-yl 2,4,6-triisopropylbenzenesulfonate

There total 3 articles about 2-amino-9-{(2R,4S,5R)-4-(tert-butyldimethylsilyloxy)-5-[(tert-butyldimethylsilyloxy)methyl]tetrahydrofuran-2-yl}-9H-purine-6-yl 2,4,6-triisopropylbenzenesulfonate 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: 94.0%

2,4,6-triisopropylphenylsulfonyl chloride (6553-96-4) + 3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine (51549-35-0) → 2-amino-9-{(2R,4S,5R)-4-(tert-butyldimethylsilyloxy)-5-[(tert-butyldimethylsilyloxy)methyl]tetrahydrofuran-2-yl}-9H-purine-6-yl 2,4,6-triisopropylbenzenesulfonate (328238-59-1)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 48h;

DOI:10.1016/j.bmc.2014.01.024

Reference yield:

2'-Deoxyguanosine (961-07-9) → 2-amino-9-{(2R,4S,5R)-4-(tert-butyldimethylsilyloxy)-5-[(tert-butyldimethylsilyloxy)methyl]tetrahydrofuran-2-yl}-9H-purine-6-yl 2,4,6-triisopropylbenzenesulfonate (328238-59-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1H-imidazole / N,N-dimethyl-formamide / 24 h

2: triethylamine; dmap / dichloromethane / 48 h / 20 °C

With 1H-imidazole; dmap; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2014.01.024

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 2-amino-9-{(2R,4S,5R)-4-(tert-butyldimethylsilyloxy)-5-[(tert-butyldimethylsilyloxy)methyl]tetrahydrofuran-2-yl}-9H-purine-6-yl 2,4,6-triisopropylbenzenesulfonate (328238-59-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1H-imidazole / N,N-dimethyl-formamide / 20 h / 20 °C / Inert atmosphere

2: dmap; triethylamine / dichloromethane; acetonitrile / 27 h / 0 °C / Inert atmosphere

With 1H-imidazole; dmap; triethylamine; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

upstream raw materials:

2,4,6-triisopropylphenylsulfonyl chloride

3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine

2'-Deoxyguanosine

tert-butyldimethylsilyl chloride

Downstream raw materials:

2'-deoxy-6-N-{2-[(1,3-diaza-3-methyl-2-oxophenoxazin-9-yl)oxy]ethyl}-2-(phenoxyacetylamino)adenosine

2′-deoxy-5’-O-(4,4'-dimethoxytrityl)-6-N-{2-[(1,3-diaza-3-methyl-2-oxophenoxazin-9-yl)oxy]ethyl}-2-(phenoxyacetylamino)adenosin-3′-yl 2-cyanoethyl N,N-diisopropylphosphoramidite

C₄₃H₅₉N₉O₈Si₂

C₅₂H₄₉N₉O₁₀