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

Base Information

• Chemical Name: allyl methyl (R_P)-2'-deoxy-5'-O-(p,p'-dimethoxytrityl)thymidin-3'-yl phosphorothioate
• CAS No.: 910213-67-1
• Molecular Formula: C₃₅H₃₉N₂O₉PS
• Molecular Weight: 694.742

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

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

Chemical Property:

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

There total 3 articles about allyl methyl (R_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: 91.0%

allyl methyl (RP)-2'-deoxythymidin-3'-yl phosphorothioate (910213-61-5) + 4,4'-dimethoxytrityl chloride (40615-36-9) → allyl methyl (RP)-2'-deoxy-5'-O-(p,p'-dimethoxytrityl)thymidin-3'-yl phosphorothioate (910213-67-1)

Guidance literature:

In pyridine; N,N-dimethyl-formamide; at 25 ℃; for 7h;

DOI:10.1002/ejoc.200600155

Reference yield:

allyl (RP)-2'-deoxythymidine 3',5'-cyclic phosphorothioate (910213-57-9) → allyl methyl (RP)-2'-deoxy-5'-O-(p,p'-dimethoxytrityl)thymidin-3'-yl phosphorothioate (910213-67-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / sodium methoxide / 24 h / 25 °C

2: 91 percent / dimethylformamide; pyridine / 7 h / 25 °C

With sodium methylate; In pyridine; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.200600155

Reference yield:

thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4) → allyl methyl (RP)-2'-deoxy-5'-O-(p,p'-dimethoxytrityl)thymidin-3'-yl phosphorothioate (910213-67-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 1H-tetrazole / acetonitrile; CH₂Cl₂ / 0 - 55 °C

1.2: 79 percent / bis[3'-(triethoxysilyl)propyl] tetrasulfide / acetonitrile; CH₂Cl₂ / 2 h / 25 °C

2.1: 83 percent / sodium methoxide / 24 h / 25 °C

3.1: 91 percent / dimethylformamide; pyridine / 7 h / 25 °C

With 1H-tetrazole; sodium methylate; In pyridine; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/ejoc.200600155

upstream raw materials:

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

4,4'-dimethoxytrityl chloride

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

thymidine

Downstream raw materials:

C₅₃H₆₇N₅O₁₄P₂S

C₅₁H₆₅N₅O₁₄P₂S

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

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

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