5'-O-(tert-butyldiphenylsilyl)-3'-deoxy-3'-C-(acetoxymethyl)-thymidine

Base Information

• Chemical Name: 5'-O-(tert-butyldiphenylsilyl)-3'-deoxy-3'-C-(acetoxymethyl)-thymidine
• CAS No.: 166955-34-6
• Molecular Formula: C₂₉H₃₆N₂O₆Si
• Molecular Weight: 536.7
• Mol file: 166955-34-6.mol

Synonyms:5'-O-(tert-butyldiphenylsilyl)-3'-deoxy-3'-C-(acetoxymethyl)-thymidine

Chemical Property of 5'-O-(tert-butyldiphenylsilyl)-3'-deoxy-3'-C-(acetoxymethyl)-thymidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5'-O-(tert-butyldiphenylsilyl)-3'-deoxy-3'-C-(acetoxymethyl)-thymidine

There total 3 articles about 5'-O-(tert-butyldiphenylsilyl)-3'-deoxy-3'-C-(acetoxymethyl)-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: 81.0%

1-{(3'R,4'S)-5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-3'-C-(hydroxymethyl)-β-pentofuranosyl}thymine (146557-80-4) → 5'-O-(tert-butyldiphenylsilyl)-3'-deoxy-3'-C-(acetoxymethyl)-thymidine (166955-34-6)

Guidance literature:

With acetic anhydride; In pyridine; hexane; ethyl acetate;

Reference yield: 81.0%

acetic anhydride (108-24-7) + 1-{(3'R,4'S)-5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-3'-C-(hydroxymethyl)-β-pentofuranosyl}thymine (146557-80-4) → 5'-O-(tert-butyldiphenylsilyl)-3'-deoxy-3'-C-(acetoxymethyl)-thymidine (166955-34-6)

Guidance literature:

In pyridine; for 24h; Ambient temperature;

DOI:10.1080/07328319608002438

Reference yield:

1-[5-(tert-butyldiphenylsilyl)-2,3-dideoxy-3-C-(formyl)-β-D-erythro-pentofuranosyl]thymine (146557-69-9) → 5'-O-(tert-butyldiphenylsilyl)-3'-deoxy-3'-C-(acetoxymethyl)-thymidine (166955-34-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / NaBH₄ / aq. ethanol / 2 h / 0 deg C -> rt

2: 81 percent / pyridine / 24 h / Ambient temperature

With sodium tetrahydroborate; In pyridine; ethanol;

DOI:10.1080/07328319608002438

upstream raw materials:

acetic anhydride

1-{(3'R,4'S)-5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-3'-C-(hydroxymethyl)-β-pentofuranosyl}thymine

1-[5-(tert-butyldiphenylsilyl)-2,3-dideoxy-3-C-(formyl)-β-D-erythro-pentofuranosyl]thymine

Downstream raw materials:

5'-O-Dimethoxytrityl-3'-acetoxymethyl-3'-deoxy-thymidine

5'-O-dimethoxytrityl-3'-hydroxymethyl-3'-deoxy-thymidine