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

Base Information

• Chemical Name: 3'-O-(acetyl)-2'-deoxythymidin-5'-yl (R_P)-2'-deoxy-5'-O-(p,p'-dimethoxytrityl)thymidin-3'-yl methyl phosphorothioate
• CAS No.: 130451-29-5
• Molecular Formula: C₄₄H₄₉N₄O₁₄PS
• Molecular Weight: 920.931

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

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

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

There total 5 articles about 3'-O-(acetyl)-2'-deoxythymidin-5'-yl (R_P)-2'-deoxy-5'-O-(p,p'-dimethoxytrityl)thymidin-3'-yl methyl 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: 62.0%

SP [triethylammonium methyl 5'-O-(p,p'-dimethoxytrityl)-2'-deoxythymidin-3'-yl phosphorothioate] + 3'-O-acetylthymidine (21090-30-2) → C44H49N4O14PS + 3'-O-(acetyl)-2'-deoxythymidin-5'-yl (RP)-2'-deoxy-5'-O-(p,p'-dimethoxytrityl)thymidin-3'-yl methyl phosphorothioate (130451-29-5)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; toluene; at 60 ℃; for 3h;

DOI:10.1002/ejoc.200600155

Reference yield:

allyl (RP)-2'-deoxythymidine 3',5'-cyclic phosphorothioate (910213-57-9) → 3'-O-(acetyl)-2'-deoxythymidin-5'-yl (RP)-2'-deoxy-5'-O-(p,p'-dimethoxytrityl)thymidin-3'-yl methyl phosphorothioate (130451-29-5)

Guidance literature:

Multi-step reaction with 4 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

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium methylate; N-butylamine; triphenylphosphine; diethylazodicarboxylate; formic acid; In tetrahydrofuran; pyridine; 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) → 3'-O-(acetyl)-2'-deoxythymidin-5'-yl (RP)-2'-deoxy-5'-O-(p,p'-dimethoxytrityl)thymidin-3'-yl methyl phosphorothioate (130451-29-5)

Guidance literature:

Multi-step reaction with 3 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

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

DOI:10.1002/ejoc.200600155

upstream raw materials:

3'-O-acetylthymidine

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

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

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