(R_P)-N⁶-benzoyl-5'-O-(4,4-dimethoxytrityl)-2'-adenoylyl-(3'->5')-N⁶-benzoyl-3'-O-<1,1-dimethylethyl)dimethylsilyl>-2'-deoxyadenosine 3'-methylphosphonate

Base Information

• Chemical Name: (R_P)-N⁶-benzoyl-5'-O-(4,4-dimethoxytrityl)-2'-adenoylyl-(3'->5')-N⁶-benzoyl-3'-O-<1,1-dimethylethyl)dimethylsilyl>-2'-deoxyadenosine 3'-methylphosphonate
• CAS No.: 133471-18-8
• Molecular Formula: C₆₂H₆₇N₁₀O₁₁PSi
• Molecular Weight: 1187.33

Synonyms:

Chemical Property of (R_P)-N⁶-benzoyl-5'-O-(4,4-dimethoxytrityl)-2'-adenoylyl-(3'->5')-N⁶-benzoyl-3'-O-<1,1-dimethylethyl)dimethylsilyl>-2'-deoxyadenosine 3'-methylphosphonate

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Technology Process of (R_P)-N⁶-benzoyl-5'-O-(4,4-dimethoxytrityl)-2'-adenoylyl-(3'->5')-N⁶-benzoyl-3'-O-<1,1-dimethylethyl)dimethylsilyl>-2'-deoxyadenosine 3'-methylphosphonate

There total 2 articles about (R_P)-N⁶-benzoyl-5'-O-(4,4-dimethoxytrityl)-2'-adenoylyl-(3'->5')-N⁶-benzoyl-3'-O-<1,1-dimethylethyl)dimethylsilyl>-2'-deoxyadenosine 3'-methylphosphonate 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:

(RP)-N6-benzoyl-5'-O-(4,4-dimethoxytrityl)-2'-deoxyadenoylyl-(3'->5')-N6-benzoyl-3'-O-<1,1-dimethylethyl)dimethylsilyl>-2'-deoxyadenosine 3'-H-phosphonate (133471-11-1,133574-72-8) + methyl iodide (74-88-4) → (RP)-N6-benzoyl-5'-O-(4,4-dimethoxytrityl)-2'-adenoylyl-(3'->5')-N6-benzoyl-3'-O-<1,1-dimethylethyl)dimethylsilyl>-2'-deoxyadenosine 3'-methylphosphonate (133471-18-8)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; multistep reaction; diastereochemistry;

DOI:10.1021/jo00012a017

Reference yield:

C45H51N6O6P (114079-05-9) + 6-N-benzoyl-3'-O-(tert-butyldimethylsilyl)-2'-deoxyadenosine (51549-40-7) → (RP)-N6-benzoyl-5'-O-(4,4-dimethoxytrityl)-2'-adenoylyl-(3'->5')-N6-benzoyl-3'-O-<1,1-dimethylethyl)dimethylsilyl>-2'-deoxyadenosine 3'-methylphosphonate (133471-18-8) + (SP)-N6-benzoyl-5'-O-(4,4-dimethoxytrityl)-2'-adenoylyl-(3'->5')-N6-benzoyl-3'-O-<1,1-dimethylethyl)dimethylsilyl>-2'-deoxyadenosine 3'-methylphosphonate (133574-79-5)

Guidance literature:

With 1H-tetrazole; tert.-butylhydroperoxide; Yield given. Multistep reaction. Yields of byproduct given; 1.) CH₃CN, room temperature, 15 min, 2.) room temperature, 10 min;

DOI:10.1080/15257779508012479

Reference yield: 62.0%

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) + (RP)-N6-benzoyl-5'-O-(4,4-dimethoxytrityl)-2'-adenoylyl-(3'->5')-N6-benzoyl-3'-O-<1,1-dimethylethyl)dimethylsilyl>-2'-deoxyadenosine 3'-methylphosphonate (133471-18-8) → N6-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenoylyl-(3'->5')-N6-benzoyl-3'-O-<(2-cyanoethyl)-N,N-diisopropylamido-phosphoramidite>-2'-deoxyadenosine 3'-(Rp)-methylphosphonate

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1080/15257779508012479

upstream raw materials:

(R_P)-N⁶-benzoyl-5'-O-(4,4-dimethoxytrityl)-2'-deoxyadenoylyl-(3'->5')-N⁶-benzoyl-3'-O-<1,1-dimethylethyl)dimethylsilyl>-2'-deoxyadenosine 3'-H-phosphonate

methyl iodide

C₄₅H₅₁N₆O₆P

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

Downstream raw materials:

(R)-Methyl-phosphonic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yl ester (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester

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