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

Base Information

• Chemical Name: 1-(3'-deoxy-5'-O-DMT-2'-O,4'-C-methylenethymidin-3'-yl)-4-(5-deoxy-3-O-tert-butyldiphenylsilyl-2-O,4-C-methylene-thymidin-5-yl)mercaptoacetamide
• CAS No.: 1430073-69-0
• Molecular Formula: C₆₁H₆₅N₅O₁₃SSi
• Molecular Weight: 1136.36
• Mol file: 1430073-69-0.mol

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

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

There total 10 articles about 1-(3'-deoxy-5'-O-DMT-2'-O,4'-C-methylenethymidin-3'-yl)-4-(5-deoxy-3-O-tert-butyldiphenylsilyl-2-O,4-C-methylene-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: 62.0%

2-S-(5'-deoxy-3'-O-tert-butyldiphenylsilyl-2'-O,4'-C-methylenethymidin-5'-yl)mercaptoacetic acid (1430073-65-6) + 3'-amino-3'-deoxy-5'-O-DMT-2'-O-4'-C-methylenethymidine (321882-29-5) → 1-(3'-deoxy-5'-O-DMT-2'-O,4'-C-methylenethymidin-3'-yl)-4-(5-deoxy-3-O-tert-butyldiphenylsilyl-2-O,4-C-methylene-thymidin-5-yl)mercaptoacetamide (1430073-69-0)

Guidance literature:

2-S-(5'-deoxy-3'-O-tert-butyldiphenylsilyl-2'-O,4'-C-methylenethymidin-5'-yl)mercaptoacetic acid; With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 25 ℃; for 0.25h;

3'-amino-3'-deoxy-5'-O-DMT-2'-O-4'-C-methylenethymidine; In N,N-dimethyl-formamide; at 25 ℃; for 4h;

DOI:10.1080/15257770.2013.783218

Reference yield:

(1S,3R,4R,7S)-7-hydroxy-1-hydroxymethyl-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane (206055-67-6) → 1-(3'-deoxy-5'-O-DMT-2'-O,4'-C-methylenethymidin-3'-yl)-4-(5-deoxy-3-O-tert-butyldiphenylsilyl-2-O,4-C-methylene-thymidin-5-yl)mercaptoacetamide (1430073-69-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: pyridine / 8 h / 0 - 20 °C

2.1: 1H-imidazole / N,N-dimethyl-formamide / 6 h / 20 °C / Inert atmosphere

3.1: sodium hydride / N,N-dimethyl-formamide; hexane / 0.5 h

3.2: 1 h / 0 - 20 °C

4.1: sodium hydroxide / methanol / 0.5 h

5.1: 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

5.2: 4 h / 25 °C

With pyridine; 1H-imidazole; sodium hydride; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In methanol; hexane; N,N-dimethyl-formamide;

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-(5-deoxy-3-O-tert-butyldiphenylsilyl-2-O,4-C-methylene-thymidin-5-yl)mercaptoacetamide (1430073-69-0)

Guidance literature:

Multi-step reaction with 3 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

With pyridine; ammonia; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In 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

2-S-(5'-deoxy-3'-O-tert-butyldiphenylsilyl-2'-O,4'-C-methylenethymidin-5'-yl)mercaptoacetic acid

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

(1S,3R,4R,7S)-7-hydroxy-1-hydroxymethyl-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

Downstream raw materials:

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