3'-N-[N-allyloxycarbonyl-S-(tert-butylthio)-L-cysteinyl]-5'-O-(tert-butyldimethylsilyl)-N6,N6-{2-[3-oxo-3-(pentafluorophenyloxy)propyl]}glutaryl-9-(3'-amino-2',3'-dideoxy-β-D-ribofuranosyl)adenine

Base Information

Chemical Name:3'-N-[N-allyloxycarbonyl-S-(tert-butylthio)-L-cysteinyl]-5'-O-(tert-butyldimethylsilyl)-N6,N6-{2-[3-oxo-3-(pentafluorophenyloxy)propyl]}glutaryl-9-(3'-amino-2',3'-dideoxy-β-D-ribofuranosyl)adenine
CAS No.:1345543-68-1
Molecular Formula:C₄₁H₅₂F₅N₇O₉S₂Si
Molecular Weight:974.115
Hs Code.:

3'-N-[N-allyloxycarbonyl-S-(tert-butylthio)-L-cysteinyl]-5'-O-(tert-butyldimethylsilyl)-N6,N6-{2-[3-oxo-3-(pentafluorophenyloxy)propyl]}glutaryl-9-(3'-amino-2',3'-dideoxy-β-D-ribofuranosyl)adenine

Synonyms:3'-N-[N-allyloxycarbonyl-S-(tert-butylthio)-L-cysteinyl]-5'-O-(tert-butyldimethylsilyl)-N6,N6-{2-[3-oxo-3-(pentafluorophenyloxy)propyl]}glutaryl-9-(3'-amino-2',3'-dideoxy-β-D-ribofuranosyl)adenine

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Chemical Property of 3'-N-[N-allyloxycarbonyl-S-(tert-butylthio)-L-cysteinyl]-5'-O-(tert-butyldimethylsilyl)-N6,N6-{2-[3-oxo-3-(pentafluorophenyloxy)propyl]}glutaryl-9-(3'-amino-2',3'-dideoxy-β-D-ribofuranosyl)adenine

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Technology Process of 3'-N-[N-allyloxycarbonyl-S-(tert-butylthio)-L-cysteinyl]-5'-O-(tert-butyldimethylsilyl)-N6,N6-{2-[3-oxo-3-(pentafluorophenyloxy)propyl]}glutaryl-9-(3'-amino-2',3'-dideoxy-β-D-ribofuranosyl)adenine

There total 6 articles about 3'-N-[N-allyloxycarbonyl-S-(tert-butylthio)-L-cysteinyl]-5'-O-(tert-butyldimethylsilyl)-N6,N6-{2-[3-oxo-3-(pentafluorophenyloxy)propyl]}glutaryl-9-(3'-amino-2',3'-dideoxy-β-D-ribofuranosyl)adenine 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: 45.0%

: 771-61-9
2,3,4,5,6-pentafluorophenol

: 1345543-67-0
3'-N-[N-allyloxycarbonyl-S-(tert-butylthio)-L-cysteinyl]-5'-O-(tert-butyldimethylsilyl)-N6,N6-{2-[3-(2-carboxyethyl)]glutaryl}-9-(3'-amino-2',3'-dideoxy-β-D-ribofuranosyl)adenine

: 1345543-68-1
3'-N-[N-allyloxycarbonyl-S-(tert-butylthio)-L-cysteinyl]-5'-O-(tert-butyldimethylsilyl)-N6,N6-{2-[3-oxo-3-(pentafluorophenyloxy)propyl]}glutaryl-9-(3'-amino-2',3'-dideoxy-β-D-ribofuranosyl)adenine

Guidance literature:: With benzotriazol-1-ol; diisopropyl-carbodiimide; In dichloromethane; at 20 ℃; for 16h; Inert atmosphere;
DOI:10.1021/ja209053b

Reference yield:

: 1345543-65-8
N-allyloxycarbonyl-S-(tert-butylthio)-L-cysteine pentafluorophenyl ester

: 1345543-68-1
3'-N-[N-allyloxycarbonyl-S-(tert-butylthio)-L-cysteinyl]-5'-O-(tert-butyldimethylsilyl)-N6,N6-{2-[3-oxo-3-(pentafluorophenyloxy)propyl]}glutaryl-9-(3'-amino-2',3'-dideoxy-β-D-ribofuranosyl)adenine

Guidance literature:: Multi-step reaction with 3 steps

1.1: pyridine / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

1.2: 24 h / 20 °C / Inert atmosphere

2.1: pyridine / 6 h / 90 °C / Inert atmosphere

3.1: benzotriazol-1-ol; diisopropyl-carbodiimide / dichloromethane / 16 h / 20 °C / Inert atmosphere

With pyridine; benzotriazol-1-ol; diisopropyl-carbodiimide; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja209053b

Reference yield:

: 30044-51-0
S-tert-butylmercapto-L-cysteine

: 1345543-68-1
3'-N-[N-allyloxycarbonyl-S-(tert-butylthio)-L-cysteinyl]-5'-O-(tert-butyldimethylsilyl)-N6,N6-{2-[3-oxo-3-(pentafluorophenyloxy)propyl]}glutaryl-9-(3'-amino-2',3'-dideoxy-β-D-ribofuranosyl)adenine

Guidance literature:: Multi-step reaction with 5 steps

1.1: sodium carbonate / tetrahydrofuran; water / 16 h / 0 - 20 °C

2.1: dmap; diisopropyl-carbodiimide / dichloromethane / 16 h / 0 - 20 °C

3.1: pyridine / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

3.2: 24 h / 20 °C / Inert atmosphere

4.1: pyridine / 6 h / 90 °C / Inert atmosphere

5.1: benzotriazol-1-ol; diisopropyl-carbodiimide / dichloromethane / 16 h / 20 °C / Inert atmosphere

With pyridine; dmap; sodium carbonate; benzotriazol-1-ol; diisopropyl-carbodiimide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/ja209053b