5'-O-(tert-butyldimethylsilyl)-3'-O-methyl-6-N-p-anisoyladenosine 2'-O-(2,2,2-trichloroethyl 2-chlorophenylphosphate)

Base Information

• Chemical Name: 5'-O-(tert-butyldimethylsilyl)-3'-O-methyl-6-N-p-anisoyladenosine 2'-O-(2,2,2-trichloroethyl 2-chlorophenylphosphate)
• CAS No.: 77057-93-3
• Molecular Formula: C₃₃H₄₀Cl₄N₅O₉PSi
• Molecular Weight: 851.58

Synonyms:5'-O-(tert-butyldimethylsilyl)-3'-O-methyl-6-N-p-anisoyladenosine 2'-O-(2,2,2-trichloroethyl 2-chlorophenylphosphate)

Chemical Property of 5'-O-(tert-butyldimethylsilyl)-3'-O-methyl-6-N-p-anisoyladenosine 2'-O-(2,2,2-trichloroethyl 2-chlorophenylphosphate)

Chemical Property:

Purity/Quality:

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Technology Process of 5'-O-(tert-butyldimethylsilyl)-3'-O-methyl-6-N-p-anisoyladenosine 2'-O-(2,2,2-trichloroethyl 2-chlorophenylphosphate)

There total 6 articles about 5'-O-(tert-butyldimethylsilyl)-3'-O-methyl-6-N-p-anisoyladenosine 2'-O-(2,2,2-trichloroethyl 2-chlorophenylphosphate) 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: 75.0%

2,2,2-trichloroethyl 2-chlorophenyl phosphorochloridate (59819-52-2) + 5'-O-(tert-butyldimethylsilyl)-3'-O-methyl-6-N-p-anisoyladenosine (76991-47-4) → 5'-O-(tert-butyldimethylsilyl)-3'-O-methyl-6-N-p-anisoyladenosine 2'-O-(2,2,2-trichloroethyl 2-chlorophenylphosphate) (77057-93-3)

Guidance literature:

With 1-methyl-1H-imidazole; In acetonitrile; at 0 ℃; for 0.75h;

DOI:10.1021/jo00324a010

Reference yield:

3'-O-methyl-2',5'-diacetyladenosine (72560-72-6) → 5'-O-(tert-butyldimethylsilyl)-3'-O-methyl-6-N-p-anisoyladenosine 2'-O-(2,2,2-trichloroethyl 2-chlorophenylphosphate) (77057-93-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) pyridine, 2.) CH₃ONa / 1.) 20 deg C, 16 h, 2.) methanol, dioxane, 15 min

2: 88 percent / pyridine / 16 h / 20 °C

3: 75 percent / 1-methylimidazole / acetonitrile / 0.75 h / 0 °C

With pyridine; 1-methyl-1H-imidazole; sodium methylate; In acetonitrile;

DOI:10.1021/jo00324a010

Reference yield:

3'-O-methyl-6-N-p-anisoyladenosine (72351-35-0) → 5'-O-(tert-butyldimethylsilyl)-3'-O-methyl-6-N-p-anisoyladenosine 2'-O-(2,2,2-trichloroethyl 2-chlorophenylphosphate) (77057-93-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / pyridine / 16 h / 20 °C

2: 75 percent / 1-methylimidazole / acetonitrile / 0.75 h / 0 °C

With pyridine; 1-methyl-1H-imidazole; In acetonitrile;

DOI:10.1021/jo00324a010

upstream raw materials:

2,2,2-trichloroethyl 2-chlorophenyl phosphorochloridate

5'-O-(tert-butyldimethylsilyl)-3'-O-methyl-6-N-p-anisoyladenosine

3'-O-methyl-2',5'-diacetyladenosine

3'-O-methyl-6-N-p-anisoyladenosine

Downstream raw materials:

Phosphoric acid (2R,3R,4R,5R)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-methoxy-2-[6-(4-methoxy-benzoylamino)-purin-9-yl]-tetrahydro-furan-3-yl ester 2-chloro-phenyl ester

3'-O-methyl-6-N-p-anisoyladenosine 2'-O-(2,2,2-trichloroethyl 2-chlorophenylphosphate)

C₅₈H₆₃Cl₅N₁₀O₁₇P₂Si

C₅₆H₆₂Cl₂N₁₀O₁₇P₂Si

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