Rp-3'-O-(tert-butyldimethylsilyl)thymidin-5'-yl 5'-O-dimethoxytritylthymidin-3'-yl phenylphosphonate

Base Information

• Chemical Name: Rp-3'-O-(tert-butyldimethylsilyl)thymidin-5'-yl 5'-O-dimethoxytritylthymidin-3'-yl phenylphosphonate
• CAS No.: 160343-11-3
• Molecular Formula: C₅₃H₆₃N₄O₁₃PSi
• Molecular Weight: 1023.16

Synonyms:Rp-3'-O-(tert-butyldimethylsilyl)thymidin-5'-yl 5'-O-dimethoxytritylthymidin-3'-yl phenylphosphonate

Chemical Property of Rp-3'-O-(tert-butyldimethylsilyl)thymidin-5'-yl 5'-O-dimethoxytritylthymidin-3'-yl phenylphosphonate

Chemical Property:

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Technology Process of Rp-3'-O-(tert-butyldimethylsilyl)thymidin-5'-yl 5'-O-dimethoxytritylthymidin-3'-yl phenylphosphonate

There total 2 articles about Rp-3'-O-(tert-butyldimethylsilyl)thymidin-5'-yl 5'-O-dimethoxytritylthymidin-3'-yl phenylphosphonate 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: 81.0%

iodobenzene (591-50-4) + (RP)-5'-O-(4,4-dimethoxytrityl)-2'-thymidylyl-(3'->5')-3'-O-<1,1-dimethylethyl)dimethylsilyl>-thymidine 3'-H-phosphonate (133471-17-7,133574-78-4,252897-94-2) → Rp-3'-O-(tert-butyldimethylsilyl)thymidin-5'-yl 5'-O-dimethoxytritylthymidin-3'-yl phenylphosphonate (160343-11-3)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; In tetrahydrofuran; at 120 ℃; for 0.166667h; stereospecific reaction; Inert atmosphere; Microwave irradiation;

DOI:10.1021/ol801935r

Reference yield: 63.0%

bromobenzene (108-86-1,52753-63-6) + (RP)-5'-O-(4,4-dimethoxytrityl)-2'-thymidylyl-(3'->5')-3'-O-<1,1-dimethylethyl)dimethylsilyl>-thymidine 3'-H-phosphonate (133471-17-7,133574-78-4,252897-94-2) → Rp-3'-O-(tert-butyldimethylsilyl)thymidin-5'-yl 5'-O-dimethoxytritylthymidin-3'-yl phenylphosphonate (160343-11-3)

Guidance literature:

With 1,1'-bis-(diphenylphosphino)ferrocene; potassium acetate; palladium diacetate; triethylamine; In tetrahydrofuran; at 68 ℃; for 5.5h; stereospecific reaction; Inert atmosphere;

DOI:10.1002/adsc.200900590

Reference yield: 89.0%

Rp-3'-O-(tert-butyldimethylsilyl)thymidin-5'-yl 5'-O-dimethoxytritylthymidin-3'-yl phenylphosphonate (160343-11-3) → (R)-5'-O-(4,4'-dimethoxytrityl)thymidin-3'-yl thymidin-5'-yl phenylphosphonate (160400-84-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 0.333333h;

upstream raw materials:

iodobenzene

(R_P)-5'-O-(4,4-dimethoxytrityl)-2'-thymidylyl-(3'->5')-3'-O-<1,1-dimethylethyl)dimethylsilyl>-thymidine 3'-H-phosphonate

bromobenzene

Downstream raw materials:

(R)-5'-O-(4,4'-dimethoxytrityl)thymidin-3'-yl thymidin-5'-yl phenylphosphonate

C₅₆H₆₆N₆O₁₄P₂

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