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

Base Information

• Chemical Name: 3'-O-tert-butyldiphenylsilyl-5'-C(S)-methyl ethanoate-thymidine
• CAS No.: 494798-45-7
• Molecular Formula: C₂₉H₃₆N₂O₇Si
• Molecular Weight: 552.7
• Mol file: 494798-45-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about 3'-O-tert-butyldiphenylsilyl-5'-C(S)-methyl ethanoate-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: 90.0%

1-(2-deoxy-3-O-tert-butyldiphenylsilyl-β-D-erythro-pentadialdo-1,4-furanosyl)-5-methyluracil (146604-43-5) → 3'-O-tert-butyldiphenylsilyl-5'-C(S)-methyl ethanoate-thymidine (494798-45-7)

Guidance literature:

With bismuth(III) chloride; zinc(II) iodide; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1021/ol027222h

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → 3'-O-tert-butyldiphenylsilyl-5'-C(S)-methyl ethanoate-thymidine (494798-45-7)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine; tert-butyldimethylsilyl chloride

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

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

With pyridine; dichloro-acetic acid; bismuth(III) chloride; tert-butyldimethylsilyl chloride; dimethyl sulfoxide; dicyclohexyl-carbodiimide; zinc(II) iodide; In dichloromethane; 2: Pfitzner-Moffatt oxidation / 3: Mukaiyama reaction;

DOI:10.1002/ejoc.201101353

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)-methyl ethanoate-thymidine (494798-45-7)

Guidance literature:

Multi-step reaction with 2 steps

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

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

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

DOI:10.1002/ejoc.201101353

upstream raw materials:

1-(2-deoxy-3-O-tert-butyldiphenylsilyl-β-D-erythro-pentadialdo-1,4-furanosyl)-5-methyluracil

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

tert-butylchlorodiphenylsilane

thymidine

Downstream raw materials:

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

C₆₉H₇₆N₅O₁₇PSSi

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