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

Base Information

• Chemical Name: 3'-O-(acetyl)-2'-deoxythymidin-5'-yl allyl (S_P)-2'-deoxy-5'-O-(p,p'-dimethoxytrityl)thymidin-3'-yl phosphorothioate
• CAS No.: 910213-84-2
• Molecular Formula: C₄₆H₅₁N₄O₁₄PS
• Molecular Weight: 946.969

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

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

Chemical Property:

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

There total 5 articles about 3'-O-(acetyl)-2'-deoxythymidin-5'-yl allyl (S_P)-2'-deoxy-5'-O-(p,p'-dimethoxytrityl)thymidin-3'-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: 54.0%

RP [triethylammonium allyl 5'-O-(p,p'-dimethoxytrityl)-2'-deoxythymidin-3'-yl phosphorothioate] + 3'-O-acetylthymidine (21090-30-2) → C46H51N4O14PS + 3'-O-(acetyl)-2'-deoxythymidin-5'-yl allyl (SP)-2'-deoxy-5'-O-(p,p'-dimethoxytrityl)thymidin-3'-yl phosphorothioate (910213-84-2)

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 allyl (SP)-2'-deoxy-5'-O-(p,p'-dimethoxytrityl)thymidin-3'-yl phosphorothioate (910213-84-2)

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: various solvent(s) / 24 h / 35 °C

3.2: 92 percent / CH₂Cl₂; H₂O

4.1: 54 percent / triphenylphosphane; DEAD / tetrahydrofuran; toluene / 3 h / 60 °C

With sodium methylate; triphenylphosphine; diethylazodicarboxylate; 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 allyl (SP)-2'-deoxy-5'-O-(p,p'-dimethoxytrityl)thymidin-3'-yl phosphorothioate (910213-84-2)

Guidance literature:

Multi-step reaction with 3 steps

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

2.1: various solvent(s) / 24 h / 35 °C

2.2: 92 percent / CH₂Cl₂; H₂O

3.1: 54 percent / triphenylphosphane; DEAD / tetrahydrofuran; toluene / 3 h / 60 °C

With triphenylphosphine; diethylazodicarboxylate; 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:

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

C₅₃H₆₇N₅O₁₄P₂S

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