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

Base Information

• Chemical Name: 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
• CAS No.: 1430073-73-6
• Molecular Formula: C₅₃H₆₄N₇O₁₃PS
• Molecular Weight: 1070.17

Synonyms:

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 14 articles about 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 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:

1-(3'-deoxy-5'-O-DMT-2'-O,4'-C-methylenethymidin-3'-yl)-4-(5-deoxy-β-thymidin-5-yl)mercaptoacetamide (1430073-70-3) + 2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) → 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 (1430073-73-6,1430073-74-7)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1080/15257770.2013.783218

Reference yield:

3′-azido-3′-deoxy-2′-O,4′-C-methylene-5-methyluridine (247025-17-8) → 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 (1430073-73-6,1430073-74-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: pyridine / 25 °C

2.1: pyridine; triphenylphosphine; ammonia / water / 25 °C

3.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.25 h / 25 °C

3.2: 4 h / 25 °C

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C

5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere

With pyridine; tetrabutyl ammonium fluoride; ammonia; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1080/15257770.2013.783218

Reference yield:

3'-azido-3'-deoxy-5'-O-DMT-2'-O-4'-C-methylenethymidine (321882-28-4) → 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 (1430073-73-6,1430073-74-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: pyridine; triphenylphosphine; ammonia / water / 25 °C

2.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.25 h / 25 °C

2.2: 4 h / 25 °C

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C

4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere

With pyridine; tetrabutyl ammonium fluoride; ammonia; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1080/15257770.2013.783218

upstream raw materials:

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

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

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

2-S-(5'-deoxy-3'-O-tert-butyldiphenylsilyl-β-thymidin-5'-yl)mercaptoacetic acid

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