(R_P)-2'-deoxy-5'-O-(p,p'-dimethoxytrityl)thymidin-3'-yl methyl 2'-deoxythymidin-5'-yl phosphorothioate

Base Information

• Chemical Name: (R_P)-2'-deoxy-5'-O-(p,p'-dimethoxytrityl)thymidin-3'-yl methyl 2'-deoxythymidin-5'-yl phosphorothioate
• CAS No.: 910213-99-9
• Molecular Formula: C₄₂H₄₇N₄O₁₃PS
• Molecular Weight: 878.894

Synonyms:(R_P)-2'-deoxy-5'-O-(p,p'-dimethoxytrityl)thymidin-3'-yl methyl 2'-deoxythymidin-5'-yl phosphorothioate

Chemical Property of (R_P)-2'-deoxy-5'-O-(p,p'-dimethoxytrityl)thymidin-3'-yl methyl 2'-deoxythymidin-5'-yl phosphorothioate

Chemical Property:

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Technology Process of (R_P)-2'-deoxy-5'-O-(p,p'-dimethoxytrityl)thymidin-3'-yl methyl 2'-deoxythymidin-5'-yl phosphorothioate

There total 6 articles about (R_P)-2'-deoxy-5'-O-(p,p'-dimethoxytrityl)thymidin-3'-yl methyl 2'-deoxythymidin-5'-yl phosphorothioate 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%

3'-O-(acetyl)-2'-deoxythymidin-5'-yl (RP)-2'-deoxy-5'-O-(p,p'-dimethoxytrityl)thymidin-3'-yl methyl phosphorothioate (130451-29-5) → (RP)-2'-deoxy-5'-O-(p,p'-dimethoxytrityl)thymidin-3'-yl methyl 2'-deoxythymidin-5'-yl phosphorothioate (910213-99-9)

Guidance literature:

With sodium methylate; In methanol; at 25 ℃; for 4h;

DOI:10.1002/ejoc.200600155

Reference yield:

allyl (RP)-2'-deoxythymidine 3',5'-cyclic phosphorothioate (910213-57-9) → (RP)-2'-deoxy-5'-O-(p,p'-dimethoxytrityl)thymidin-3'-yl methyl 2'-deoxythymidin-5'-yl phosphorothioate (910213-99-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 83 percent / sodium methoxide / 24 h / 25 °C

2.1: 91 percent / dimethylformamide; pyridine / 7 h / 25 °C

3.1: triphenylphosphane; Pd₂[(C₆H₅CH=CH)2CO]3*CHCl₃; butylamine / formic acid / tetrahydrofuran / 2 h / 25 °C

3.2: 88 percent / CH₂Cl₂; H₂O

4.1: 62 percent / triphenylphosphane; DEAD / tetrahydrofuran; toluene / 3 h / 60 °C

5.1: 84 percent / sodium methoxide / methanol / 4 h / 25 °C

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium methylate; N-butylamine; triphenylphosphine; diethylazodicarboxylate; formic acid; In tetrahydrofuran; pyridine; methanol; N,N-dimethyl-formamide; toluene; 4.1: Mitsunobu reaction;

DOI:10.1002/ejoc.200600155

Reference yield:

allyl methyl (RP)-2'-deoxythymidin-3'-yl phosphorothioate (910213-61-5) → (RP)-2'-deoxy-5'-O-(p,p'-dimethoxytrityl)thymidin-3'-yl methyl 2'-deoxythymidin-5'-yl phosphorothioate (910213-99-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 91 percent / dimethylformamide; pyridine / 7 h / 25 °C

2.1: triphenylphosphane; Pd₂[(C₆H₅CH=CH)2CO]3*CHCl₃; butylamine / formic acid / tetrahydrofuran / 2 h / 25 °C

2.2: 88 percent / CH₂Cl₂; H₂O

3.1: 62 percent / triphenylphosphane; DEAD / tetrahydrofuran; toluene / 3 h / 60 °C

4.1: 84 percent / sodium methoxide / methanol / 4 h / 25 °C

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium methylate; N-butylamine; triphenylphosphine; diethylazodicarboxylate; formic acid; In tetrahydrofuran; pyridine; methanol; N,N-dimethyl-formamide; toluene; 3.1: Mitsunobu reaction;

DOI:10.1002/ejoc.200600155

upstream raw materials:

3'-O-(acetyl)-2'-deoxythymidin-5'-yl (R_P)-2'-deoxy-5'-O-(p,p'-dimethoxytrityl)thymidin-3'-yl methyl phosphorothioate

allyl (R_P)-2'-deoxythymidine 3',5'-cyclic phosphorothioate

allyl methyl (R_P)-2'-deoxythymidin-3'-yl phosphorothioate

allyl methyl (R_P)-2'-deoxy-5'-O-(p,p'-dimethoxytrityl)thymidin-3'-yl phosphorothioate

Downstream raw materials:

C₅₁H₆₅N₅O₁₄P₂S

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