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

Base Information

• Chemical Name: 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
• CAS No.: 76998-95-3
• Molecular Formula: C₃₁H₃₉ClN₅O₉PSi
• Molecular Weight: 720.191

Synonyms: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

Chemical Property of 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

Chemical Property:

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Technology Process of 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

There total 8 articles about 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 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:

5'-O-(tert-butyldimethylsilyl)-3'-O-methyl-6-N-p-anisoyladenosine 2'-O-(2,2,2-trichloroethyl 2-chlorophenylphosphate) (77057-93-3) → 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 (76998-95-3)

Guidance literature:

With 2,4,6-tri(iso-propyl)benzenesulfonic acid; zinc; In pyridine; for 0.05h;

DOI:10.1021/jo00324a010

Reference yield:

2,2,2-trichloroethyl 2-chlorophenyl phosphorochloridate (59819-52-2) → 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 (76998-95-3)

Guidance literature:

Multi-step reaction with 2 steps

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

2: activ. zinc, 2,4,6-triisopropylbenzenesulfonic acid (TPSOH) / pyridine / 0.05 h

With 1-methyl-1H-imidazole; 2,4,6-tri(iso-propyl)benzenesulfonic acid; zinc; In pyridine; acetonitrile;

DOI:10.1021/jo00324a010

Reference yield:

3'-O-methyl-2',5'-diacetyladenosine (72560-72-6) → 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 (76998-95-3)

Guidance literature:

Multi-step reaction with 4 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

4: activ. zinc, 2,4,6-triisopropylbenzenesulfonic acid (TPSOH) / pyridine / 0.05 h

With pyridine; 1-methyl-1H-imidazole; 2,4,6-tri(iso-propyl)benzenesulfonic acid; sodium methylate; zinc; In pyridine; acetonitrile;

DOI:10.1021/jo00324a010

upstream raw materials:

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

2,2,2-trichloroethyl 2-chlorophenyl phosphorochloridate

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

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

Downstream raw materials:

C₅₆H₆₂Cl₂N₁₀O₁₇P₂Si

C₅₈H₆₃Cl₅N₁₀O₁₇P₂Si

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