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

Base Information

Chemical Name:ethyl [(5'S)-5'-C-(3-bromopropyl)-3'-O-(tert-butyldiphenylsilyloxy)thymidine-5'-O-yl][(5'-O-dimethoxytrityl)thymidine-3'O-yl]phosphite
CAS No.:1360614-00-1
Molecular Formula:C₆₂H₇₂BrN₄O₁₃PSi
Molecular Weight:1220.24
Hs Code.:

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

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

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

There total 6 articles about ethyl [(5'S)-5'-C-(3-bromopropyl)-3'-O-(tert-butyldiphenylsilyloxy)thymidine-5'-O-yl][(5'-O-dimethoxytrityl)thymidine-3'O-yl]phosphite 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: 92.0%

: 1360613-99-5
(5'S)-C-(bromopropyl)-3'-O-(tert-butyldiphenylsilyl)thymidine

: 5'-O-(p,p'-Dimethoxytrityl)thymidine 3'-(ethyl N,N-diisopropylphosphoroamidite)

: 1360614-00-1
ethyl [(5'S)-5'-C-(3-bromopropyl)-3'-O-(tert-butyldiphenylsilyloxy)thymidine-5'-O-yl][(5'-O-dimethoxytrityl)thymidine-3'O-yl]phosphite

Guidance literature:: With 5-ethylthiotetrazole; In acetonitrile; at 20 ℃; for 0.75h; Inert atmosphere;
DOI:10.1002/ejoc.201101061

Reference yield:

: 1360613-98-4
(5'S)-C-(bromopropyl)-3'-O-(tert-butyldiphenylsilyl)-5'-O-(trimethylsilyl)thymidine

: 1360614-00-1
ethyl [(5'S)-5'-C-(3-bromopropyl)-3'-O-(tert-butyldiphenylsilyloxy)thymidine-5'-O-yl][(5'-O-dimethoxytrityl)thymidine-3'O-yl]phosphite

Guidance literature:: Multi-step reaction with 2 steps

1: toluene-4-sulfonic acid / methanol / 1 h / 20 °C

2: 5-ethylthiotetrazole / acetonitrile / 0.75 h / 20 °C / Inert atmosphere

With 5-ethylthiotetrazole; toluene-4-sulfonic acid; In methanol; acetonitrile;
DOI:10.1002/ejoc.201101061

Reference yield:

: 244035-21-0
5'(S)-C-allyl-3'-O-(tert-butyldiphenylsilyl)thymidine

: 1360614-00-1
ethyl [(5'S)-5'-C-(3-bromopropyl)-3'-O-(tert-butyldiphenylsilyloxy)thymidine-5'-O-yl][(5'-O-dimethoxytrityl)thymidine-3'O-yl]phosphite

Guidance literature:: Multi-step reaction with 6 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

5.1: toluene-4-sulfonic acid / methanol / 1 h / 20 °C

6.1: 5-ethylthiotetrazole / acetonitrile / 0.75 h / 20 °C / Inert atmosphere

With pyridine; dimethylsulfide borane complex; 5-ethylthiotetrazole; toluene-4-sulfonic acid; lithium bromide; In tetrahydrofuran; methanol; chloroform; N,N-dimethyl-formamide; acetone; acetonitrile;
DOI:10.1002/ejoc.201101061