3'-azido-3'-deoxy-5'-O-DMT-2'-O-4'-C-methylenethymidine

Base Information

• Chemical Name: 3'-azido-3'-deoxy-5'-O-DMT-2'-O-4'-C-methylenethymidine
• CAS No.: 321882-28-4
• Molecular Formula: C₃₂H₃₁N₅O₇
• Molecular Weight: 597.627
• Mol file: 321882-28-4.mol

Synonyms:3'-azido-3'-deoxy-5'-O-DMT-2'-O-4'-C-methylenethymidine

Chemical Property of 3'-azido-3'-deoxy-5'-O-DMT-2'-O-4'-C-methylenethymidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3'-azido-3'-deoxy-5'-O-DMT-2'-O-4'-C-methylenethymidine

There total 7 articles about 3'-azido-3'-deoxy-5'-O-DMT-2'-O-4'-C-methylenethymidine 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: 76.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + 3′-azido-3′-deoxy-2′-O,4′-C-methylene-5-methyluridine (247025-17-8) → 3'-azido-3'-deoxy-5'-O-DMT-2'-O-4'-C-methylenethymidine (321882-28-4)

Guidance literature:

With pyridine; dmap; at 20 ℃;

DOI:10.1039/b105640a

Reference yield:

thymin (65-71-4,28806-14-6,691841-57-3) → 3'-azido-3'-deoxy-5'-O-DMT-2'-O-4'-C-methylenethymidine (321882-28-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 1 h / Inert atmosphere; Reflux

1.2: 14 h / 20 °C / Inert atmosphere; Reflux

2.1: sodium hydroxide / 1,4-dioxane; water / 1 h / 20 °C

3.1: N,N-dimethyl-formamide / 4 h / 10 °C

4.1: sodium hydroxide; water / tetrahydrofuran / 1 h / 0 °C

5.1: pyridine / 25 °C

With pyridine; N,O-bis-(trimethylsilyl)-acetamide; water; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; water; N,N-dimethyl-formamide; acetonitrile; 1.1: |Vorbrueggen Nucleoside Synthesis / 1.2: |Vorbrueggen Nucleoside Synthesis;

DOI:10.1080/15257770.2013.783218

Reference yield:

3-azido-1,2-di-O-acetyl-5-O-methylsulfonyl-4-[(methylsulfonyloxy)methyl]-α,β-D-erythro-pentofuranose (474927-08-7) → 3'-azido-3'-deoxy-5'-O-DMT-2'-O-4'-C-methylenethymidine (321882-28-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 1 h / Inert atmosphere; Reflux

1.2: 14 h / 20 °C / Inert atmosphere; Reflux

2.1: sodium hydroxide / 1,4-dioxane; water / 1 h / 20 °C

3.1: N,N-dimethyl-formamide / 4 h / 10 °C

4.1: sodium hydroxide; water / tetrahydrofuran / 1 h / 0 °C

5.1: pyridine / 25 °C

With pyridine; N,O-bis-(trimethylsilyl)-acetamide; water; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; water; N,N-dimethyl-formamide; acetonitrile; 1.1: |Vorbrueggen Nucleoside Synthesis / 1.2: |Vorbrueggen Nucleoside Synthesis;

DOI:10.1080/15257770.2013.783218

upstream raw materials:

4,4'-dimethoxytrityl chloride

3′-azido-3′-deoxy-2′-O,4′-C-methylene-5-methyluridine

thymin

3-azido-1,2-di-O-acetyl-5-O-methylsulfonyl-4-[(methylsulfonyloxy)methyl]-α,β-D-erythro-pentofuranose

Downstream raw materials:

1-(3'-deoxy-5'-O-DMT-2'-O,4'-C-methylenethymidin-3'-yl)-4-(5-deoxy-3-O-tert-butyldiphenylsilyl-β-thymidin-5-yl)mercaptoacetamide

1-(3'-deoxy-5'-O-DMT-2'-O,4'-C-methylenethymidin-3'-yl)-4-(5-deoxy-β-thymidin-5-yl)mercaptoacetamide

1-(3'-deoxy-5'-O-DMT-2'-O,4'-C-methylenethymidin-3'-yl)-4-(5-deoxy-2-O,4-C-methylenethymidin-5-yl)mercaptoacetamide

1-(3'-deoxy-5'-O-DMT-2'-O,4'-C-methylenethymidin-3'-yl)-4-(3-O-β-cyanoethyl-N,N-diisopropylphosphoramidite-5-deoxy-β-thymidin-5-yl)mercaptoacetamide