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

Base Information

• Chemical Name: ethyl 2-S-(3'-O-tert-butyldiphenylsilyl-5'-deoxy-2'-O,4'-C-methylenethymidin-5'-yl)mercaptoacetate
• CAS No.: 1430073-64-5
• Molecular Formula: C₃₁H₃₈N₂O₇SSi
• Molecular Weight: 610.803
• Mol file: 1430073-64-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about ethyl 2-S-(3'-O-tert-butyldiphenylsilyl-5'-deoxy-2'-O,4'-C-methylenethymidin-5'-yl)mercaptoacetate 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: 82.0%

5'-O-p-toluenesulfonyl-3'-O-tert-butyldiphenylsilyl-2'-O,4'-C-methylenethymidine (1430073-63-4) + ethyl 2-sulfanylacetate (623-51-8) → ethyl 2-S-(3'-O-tert-butyldiphenylsilyl-5'-deoxy-2'-O,4'-C-methylenethymidin-5'-yl)mercaptoacetate (1430073-64-5)

Guidance literature:

ethyl 2-sulfanylacetate; With sodium hydride; In hexane; N,N-dimethyl-formamide; for 0.5h;

5'-O-p-toluenesulfonyl-3'-O-tert-butyldiphenylsilyl-2'-O,4'-C-methylenethymidine; In hexane; N,N-dimethyl-d₆-formamide; at 0 - 20 ℃; for 1h;

DOI:10.1080/15257770.2013.783218

Reference yield:

5'-O-p-toluenesulfonyl-2'-O,4'-C-methylenethymidine (1430073-62-3) → ethyl 2-S-(3'-O-tert-butyldiphenylsilyl-5'-deoxy-2'-O,4'-C-methylenethymidin-5'-yl)mercaptoacetate (1430073-64-5)

Guidance literature:

Multi-step reaction with 2 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

With 1H-imidazole; sodium hydride; In 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) → ethyl 2-S-(3'-O-tert-butyldiphenylsilyl-5'-deoxy-2'-O,4'-C-methylenethymidin-5'-yl)mercaptoacetate (1430073-64-5)

Guidance literature:

Multi-step reaction with 3 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

With pyridine; 1H-imidazole; sodium hydride; In 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-sulfanylacetate

Downstream raw materials:

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

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