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

Base Information

• Chemical Name: Sp-3'-O-(tert-butyldimethylsilyl)thymidin-5'-yl 5'-O-dimethoxytritylthymidin-3'-yl phenylphosphonate
• CAS No.: 160400-69-1
• Molecular Formula: C₅₃H₆₃N₄O₁₃PSi
• Molecular Weight: 1023.16

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

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

Chemical Property:

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

There total 3 articles about Sp-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: 84.0%

iodobenzene (591-50-4) + (SP)-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) → Sp-3'-O-(tert-butyldimethylsilyl)thymidin-5'-yl 5'-O-dimethoxytritylthymidin-3'-yl phenylphosphonate (160400-69-1)

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: 74.0%

iodobenzene (591-50-4) + 5'-O-(4,4'-dimethoxytrityl)thymidin-3'-yl 3'-O-(tert-butyldimethylsilyl)thymidin-5'-yl H-phosphonate (133471-17-7,133574-78-4,252897-94-2) → Sp-3'-O-(tert-butyldimethylsilyl)thymidin-5'-yl 5'-O-dimethoxytritylthymidin-3'-yl phenylphosphonate (160400-69-1)

Guidance literature:

With 1,1'-bis-(diphenylphosphino)ferrocene; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine; water; palladium diacetate; triethylamine; In tetrahydrofuran; for 3h; stereospecific reaction; Inert atmosphere; Reflux;

Reference yield: 56.0%

bromobenzene (108-86-1,52753-63-6) + (SP)-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) → Sp-3'-O-(tert-butyldimethylsilyl)thymidin-5'-yl 5'-O-dimethoxytritylthymidin-3'-yl phenylphosphonate (160400-69-1)

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

upstream raw materials:

iodobenzene

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

bromobenzene

5'-O-(4,4'-dimethoxytrityl)thymidin-3'-yl 3'-O-(tert-butyldimethylsilyl)thymidin-5'-yl H-phosphonate

Downstream raw materials:

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

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