3'-O-tert-butyldiphenylsilyl-5'-C(S)-2-hydroxyethyl-thymidine

Base Information

• Chemical Name: 3'-O-tert-butyldiphenylsilyl-5'-C(S)-2-hydroxyethyl-thymidine
• CAS No.: 494798-46-8
• Molecular Formula: C₂₈H₃₆N₂O₆Si
• Molecular Weight: 524.689
• Mol file: 494798-46-8.mol

Synonyms:3'-O-tert-butyldiphenylsilyl-5'-C(S)-2-hydroxyethyl-thymidine

Chemical Property of 3'-O-tert-butyldiphenylsilyl-5'-C(S)-2-hydroxyethyl-thymidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3'-O-tert-butyldiphenylsilyl-5'-C(S)-2-hydroxyethyl-thymidine

There total 6 articles about 3'-O-tert-butyldiphenylsilyl-5'-C(S)-2-hydroxyethyl-thymidine 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: 100.0%

3′-O-tert-butyldiphenylsilyl-5′-O-trimethylsilyl-5′-oxyethylthymidine → 3'-O-tert-butyldiphenylsilyl-5'-C(S)-2-hydroxyethyl-thymidine (494798-46-8)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; for 1h;

DOI:10.1002/ejoc.201601568

Reference yield: 85.0%

3'-O-tert-butyldiphenylsilyl-5'-C(S)-methyl ethanoate-thymidine (494798-45-7) → 3'-O-tert-butyldiphenylsilyl-5'-C(S)-2-hydroxyethyl-thymidine (494798-46-8)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at 20 ℃; for 12h;

DOI:10.1021/ol027222h

Reference yield:

1-[(2R,4S,5R)-4-(tert-butyldiphenylsilanyloxy)-5-hydroxymethyltetrahydrofuran-2-yl]-5-methyl-1H-pyrimidine-2,4-dione (83467-48-5) → 3'-O-tert-butyldiphenylsilyl-5'-C(S)-2-hydroxyethyl-thymidine (494798-46-8)

Guidance literature:

Multi-step reaction with 3 steps

1: dichloro-acetic acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide

2: bismuth(III) chloride; zinc(II) iodide / dichloromethane

3: sodium tetrahydroborate / ethanol

With dichloro-acetic acid; bismuth(III) chloride; sodium tetrahydroborate; dimethyl sulfoxide; dicyclohexyl-carbodiimide; zinc(II) iodide; In ethanol; dichloromethane; 1: Pfitzner-Moffatt oxidation / 2: Mukaiyama reaction;

DOI:10.1002/ejoc.201101353

upstream raw materials:

3'-O-tert-butyldiphenylsilyl-5'-C(S)-methyl ethanoate-thymidine

1-[(2R,4S,5R)-4-(tert-butyldiphenylsilanyloxy)-5-hydroxymethyltetrahydrofuran-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

tert-butylchlorodiphenylsilane

thymidine

Downstream raw materials:

5′-C(S)-tosyloxyethyl-3′-O-(tert-butyldiphenylsilyl)thymidine

C₆₉H₇₆N₅O₁₇PSSi