5'-O-(trimethylsilyl), 3'-O-(t-butyldiphenylsilyl)-(5S)'-C-allylthymidine

Base Information

• Chemical Name: 5'-O-(trimethylsilyl), 3'-O-(t-butyldiphenylsilyl)-(5S)'-C-allylthymidine
• CAS No.: 224157-40-8
• Molecular Formula: C₃₂H₄₄N₂O₅Si₂
• Molecular Weight: 592.883
• Mol file: 224157-40-8.mol

Synonyms:5'-O-(trimethylsilyl), 3'-O-(t-butyldiphenylsilyl)-(5S)'-C-allylthymidine

Chemical Property of 5'-O-(trimethylsilyl), 3'-O-(t-butyldiphenylsilyl)-(5S)'-C-allylthymidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5'-O-(trimethylsilyl), 3'-O-(t-butyldiphenylsilyl)-(5S)'-C-allylthymidine

There total 2 articles about 5'-O-(trimethylsilyl), 3'-O-(t-butyldiphenylsilyl)-(5S)'-C-allylthymidine 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: 95.0%

chloro-trimethyl-silane (75-77-4) + 5'(S)-C-allyl-3'-O-(tert-butyldiphenylsilyl)thymidine (244035-21-0) → 5'-O-(trimethylsilyl), 3'-O-(t-butyldiphenylsilyl)-(5S)'-C-allylthymidine (224157-40-8)

Guidance literature:

With pyridine; at 20 ℃; for 3h;

DOI:10.1002/ejoc.201101061

Reference yield:

1-(2-deoxy-3-O-tert-butyldiphenylsilyl-β-D-erythro-pentadialdo-1,4-furanosyl)-5-methyluracil (146604-43-5) → 5'-O-(trimethylsilyl), 3'-O-(t-butyldiphenylsilyl)-(5S)'-C-allylthymidine (224157-40-8)

Guidance literature:

Multi-step reaction with 2 steps

1: BF₃*Et₂O / CH₂Cl₂ / 3 h / 0 °C

2: HMDS / pyridine / 3 h / Ambient temperature

With boron trifluoride diethyl etherate; 1,1,1,3,3,3-hexamethyl-disilazane; In pyridine; dichloromethane;

DOI:10.1016/S0040-4020(99)00246-X

Reference yield: 90.0%

5'-O-(trimethylsilyl), 3'-O-(t-butyldiphenylsilyl)-(5S)'-C-allylthymidine (224157-40-8) → 5'-O-(trimethylsilyl), 3'-O-(t-butyldiphenylsilyl)-(5S)'-C-(propan-1-ol)-thymidine (224157-41-9)

Guidance literature:

5'-O-(trimethylsilyl), 3'-O-(t-butyldiphenylsilyl)-(5S)'-C-allylthymidine; With dimethylsulfide borane complex; In tetrahydrofuran; at 20 ℃; for 2h;

With dihydrogen peroxide; sodium hydroxide; In tetrahydrofuran; at 20 ℃; for 0.5h;

DOI:10.1002/ejoc.201101061

upstream raw materials:

chloro-trimethyl-silane

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

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

Downstream raw materials:

5'-O-(trimethylsilyl), 3'-O-(t-butyldiphenylsilyl)-(5S)'-C-(propan-1-ol)-thymidine

5'-O-(trimethylsilyl), 3'-O-(t-butyldiphenylsilyl)-(5S)'-C-(oxo-propan)-thymidine

3'-O-(t-butyldiphenylsilyl)-(5S)'-C-(hex-3-ene-1-ol)-thymidine

C₃₉H₄₉N₄O₁₁PSi