Phosphorous acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-ylmethyl ester dimethyl ester

Base Information

• Chemical Name: Phosphorous acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-ylmethyl ester dimethyl ester
• CAS No.: 146578-13-4
• Molecular Formula: C₂₅H₃₆N₅O₆PSi
• Molecular Weight: 561.65
• Mol file: 146578-13-4.mol

Synonyms:

Chemical Property of Phosphorous acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-ylmethyl ester dimethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Phosphorous acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-ylmethyl ester dimethyl ester

There total 5 articles about Phosphorous acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-ylmethyl ester dimethyl 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:

tert-butyldimethylsilyl chloride (18162-48-6) → Phosphorous acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-ylmethyl ester dimethyl ester (146578-13-4)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine, imidazole / 20 h / Ambient temperature

2: 72 percent / 80percent HOAc / 0.5 h / Ambient temperature

3: tetrazole / CH₂Cl₂; acetonitrile / 2 h / Ambient temperature

With pyridine; 1H-imidazole; 1H-tetrazole; acetic acid; In dichloromethane; acetonitrile;

DOI:10.1016/S0040-4039(00)60176-4

Reference yield:

5’-O-(4,4’dimethoxytrityl)-N6-(benzoyl)-3’-O-tert-butyldimethylsilyldeoxyadenosine (146578-12-3) → Phosphorous acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-ylmethyl ester dimethyl ester (146578-13-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / 80percent HOAc / 0.5 h / Ambient temperature

2: tetrazole / CH₂Cl₂; acetonitrile / 2 h / Ambient temperature

With 1H-tetrazole; acetic acid; In dichloromethane; acetonitrile;

DOI:10.1016/S0040-4039(00)60176-4

Reference yield:

N6-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine (64325-78-6) → Phosphorous acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-ylmethyl ester dimethyl ester (146578-13-4)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine, imidazole / 20 h / Ambient temperature

2: 72 percent / 80percent HOAc / 0.5 h / Ambient temperature

3: tetrazole / CH₂Cl₂; acetonitrile / 2 h / Ambient temperature

With pyridine; 1H-imidazole; 1H-tetrazole; acetic acid; In dichloromethane; acetonitrile;

DOI:10.1016/S0040-4039(00)60176-4

upstream raw materials:

dimethyl N,N-diisopropylphosphoramidite

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

tert-butyldimethylsilyl chloride

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

Downstream raw materials:

C₅₅H₆₅N₈O₁₂PSi

[(2S,3S,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-phosphoramidic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester methyl ester

C₅₈H₆₈N₁₀O₁₃P₂