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

Base Information

• Chemical Name: (5'S)-C-(bromopropyl)-3'-O-(tert-butyldiphenylsilyl)-5'-O-(trimethylsilyl)thymidine
• CAS No.: 1360613-98-4
• Molecular Formula: C₃₂H₄₅BrN₂O₅Si₂
• Molecular Weight: 673.795
• Mol file: 1360613-98-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about (5'S)-C-(bromopropyl)-3'-O-(tert-butyldiphenylsilyl)-5'-O-(trimethylsilyl)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'S)-C-(tosyloxypropyl)thymidine → (5'S)-C-(bromopropyl)-3'-O-(tert-butyldiphenylsilyl)-5'-O-(trimethylsilyl)thymidine (1360613-98-4)

Guidance literature:

With lithium bromide; In N,N-dimethyl-formamide; acetone; for 0.75h; Inert atmosphere; Reflux;

DOI:10.1002/ejoc.201101061

Reference yield:

5'(S)-C-allyl-3'-O-(tert-butyldiphenylsilyl)thymidine (244035-21-0) → (5'S)-C-(bromopropyl)-3'-O-(tert-butyldiphenylsilyl)-5'-O-(trimethylsilyl)thymidine (1360613-98-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: pyridine / 3 h / 20 °C

2.1: dimethylsulfide borane complex / tetrahydrofuran / 2 h / 20 °C

2.2: 0.5 h / 20 °C

3.1: pyridine / chloroform / 16 h / 0 - 20 °C / Inert atmosphere

4.1: lithium bromide / N,N-dimethyl-formamide; acetone / 0.75 h / Inert atmosphere; Reflux

With pyridine; dimethylsulfide borane complex; lithium bromide; In tetrahydrofuran; chloroform; N,N-dimethyl-formamide; acetone;

DOI:10.1002/ejoc.201101061

Reference yield:

5'-O-(trimethylsilyl), 3'-O-(t-butyldiphenylsilyl)-(5S)'-C-(propan-1-ol)-thymidine (224157-41-9) → (5'S)-C-(bromopropyl)-3'-O-(tert-butyldiphenylsilyl)-5'-O-(trimethylsilyl)thymidine (1360613-98-4)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / chloroform / 16 h / 0 - 20 °C / Inert atmosphere

2: lithium bromide / N,N-dimethyl-formamide; acetone / 0.75 h / Inert atmosphere; Reflux

With pyridine; lithium bromide; In chloroform; N,N-dimethyl-formamide; acetone;

DOI:10.1002/ejoc.201101061

upstream raw materials:

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

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

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

Downstream raw materials:

C₃₉H₄₉N₄O₁₁PSi

C₃₉H₄₉N₄O₁₁PSi

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

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