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

Base Information

• Chemical Name: 5'-O-(trimethylsilyl), 3'-O-(t-butyldiphenylsilyl)-(5S)'-C-(propan-1-ol)-thymidine
• CAS No.: 224157-41-9
• Molecular Formula: C₃₂H₄₆N₂O₆Si₂
• Molecular Weight: 610.898
• Mol file: 224157-41-9.mol

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

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

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-(propan-1-ol)-thymidine

There total 3 articles about 5'-O-(trimethylsilyl), 3'-O-(t-butyldiphenylsilyl)-(5S)'-C-(propan-1-ol)-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%

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

Reference yield:

5'(S)-C-allyl-3'-O-(tert-butyldiphenylsilyl)thymidine (244035-21-0) → 5'-O-(trimethylsilyl), 3'-O-(t-butyldiphenylsilyl)-(5S)'-C-(propan-1-ol)-thymidine (224157-41-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: hexamethyldisilazane; pyridine

2.1: BH₃:DMS

2.2: NaOH; H₂O₂

With pyridine; dimethylsulfide borane complex; 1,1,1,3,3,3-hexamethyl-disilazane; 1.1: Etherification / 2.1: hydroboration / 2.2: Oxidation;

DOI:10.1080/07328319908044777

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-(propan-1-ol)-thymidine (224157-41-9)

Guidance literature:

Multi-step reaction with 3 steps

1: BF₃*Et₂O / CH₂Cl₂ / 3 h / 0 °C

2: HMDS / pyridine / 3 h / Ambient temperature

3: 1.) BH₃:Me₂S, 2.) 2N NaOH, 30 percent H₂O₂ / 1.) THF, room temperature, 3 h, 2.) 15 min

With sodium hydroxide; dimethylsulfide borane complex; boron trifluoride diethyl etherate; dihydrogen peroxide; 1,1,1,3,3,3-hexamethyl-disilazane; In pyridine; dichloromethane;

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

upstream raw materials:

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

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:

ethyl [(5'S)-5'-C-(3-bromopropyl)-3'-O-(tert-butyldiphenylsilyloxy)thymidine-5'-O-yl][(5'-O-dimethoxytrityl)thymidine-3'O-yl]phosphite

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

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

C₃₉H₄₉N₄O₁₁PSi