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

Base Information

• Chemical Name: 2-S-(5'-deoxy-3'-O-tert-butyldiphenylsilyl-2'-O,4'-C-methylenethymidin-5'-yl)mercaptoacetic acid
• CAS No.: 1430073-65-6
• Molecular Formula: C₂₉H₃₄N₂O₇SSi
• Molecular Weight: 582.75
• Mol file: 1430073-65-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about 2-S-(5'-deoxy-3'-O-tert-butyldiphenylsilyl-2'-O,4'-C-methylenethymidin-5'-yl)mercaptoacetic acid 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: 94.0%

ethyl 2-S-(3'-O-tert-butyldiphenylsilyl-5'-deoxy-2'-O,4'-C-methylenethymidin-5'-yl)mercaptoacetate (1430073-64-5) → 2-S-(5'-deoxy-3'-O-tert-butyldiphenylsilyl-2'-O,4'-C-methylenethymidin-5'-yl)mercaptoacetic acid (1430073-65-6)

Guidance literature:

With sodium hydroxide; In methanol; for 0.5h;

DOI:10.1080/15257770.2013.783218

Reference yield:

5'-O-p-toluenesulfonyl-2'-O,4'-C-methylenethymidine (1430073-62-3) → 2-S-(5'-deoxy-3'-O-tert-butyldiphenylsilyl-2'-O,4'-C-methylenethymidin-5'-yl)mercaptoacetic acid (1430073-65-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 6 h / 20 °C / Inert atmosphere

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

2.2: 1 h / 0 - 20 °C

3.1: sodium hydroxide / methanol / 0.5 h

With 1H-imidazole; sodium hydride; sodium hydroxide; In methanol; hexane; N,N-dimethyl-formamide;

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) → 2-S-(5'-deoxy-3'-O-tert-butyldiphenylsilyl-2'-O,4'-C-methylenethymidin-5'-yl)mercaptoacetic acid (1430073-65-6)

Guidance literature:

Multi-step reaction with 4 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

With pyridine; 1H-imidazole; sodium hydride; sodium hydroxide; In methanol; hexane; N,N-dimethyl-formamide;

DOI:10.1080/15257770.2013.783218

upstream raw materials:

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

5'-O-p-toluenesulfonyl-2'-O,4'-C-methylenethymidine

5'-O-p-toluenesulfonyl-3'-O-tert-butyldiphenylsilyl-2'-O,4'-C-methylenethymidine

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

Downstream raw materials:

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

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