N-allyloxycarbonyl-S-(tert-butylthio)-L-cysteine pentafluorophenyl ester

Base Information

• Chemical Name: N-allyloxycarbonyl-S-(tert-butylthio)-L-cysteine pentafluorophenyl ester
• CAS No.: 1345543-65-8
• Molecular Formula: C₁₇H₁₈F₅NO₄S₂
• Molecular Weight: 459.458

Synonyms:N-allyloxycarbonyl-S-(tert-butylthio)-L-cysteine pentafluorophenyl ester

Chemical Property of N-allyloxycarbonyl-S-(tert-butylthio)-L-cysteine pentafluorophenyl ester

Chemical Property:

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Technology Process of N-allyloxycarbonyl-S-(tert-butylthio)-L-cysteine pentafluorophenyl ester

There total 2 articles about N-allyloxycarbonyl-S-(tert-butylthio)-L-cysteine pentafluorophenyl ester 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: 77.0%

N-allyloxycarbonyl-S-(tert-butylthio)-L-cysteine (854032-63-6) + 2,3,4,5,6-pentafluorophenol (771-61-9) → N-allyloxycarbonyl-S-(tert-butylthio)-L-cysteine pentafluorophenyl ester (1345543-65-8)

Guidance literature:

With dmap; diisopropyl-carbodiimide; In dichloromethane; at 0 - 20 ℃; for 16h;

DOI:10.1021/ja209053b

Reference yield:

S-tert-butylmercapto-L-cysteine (30044-51-0) → N-allyloxycarbonyl-S-(tert-butylthio)-L-cysteine pentafluorophenyl ester (1345543-65-8)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With dmap; sodium carbonate; diisopropyl-carbodiimide; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/ja209053b

Reference yield: 67.0%

N-allyloxycarbonyl-S-(tert-butylthio)-L-cysteine pentafluorophenyl ester (1345543-65-8) + 3'-amino-6-N-[(di-n-butylamino)methylene]-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-β-D-adenosine → 6-N-[(di-n-butylamino)methylene]-3'-{[N-allyloxycarbonyl-S-(tert-butylthio)-L-cysteinyl]amino}-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-β-D-adenosine

Guidance literature:

In N,N-dimethyl-formamide; at 20 ℃; for 16h; Inert atmosphere;

DOI:10.1021/ja209053b

upstream raw materials:

N-allyloxycarbonyl-S-(tert-butylthio)-L-cysteine

2,3,4,5,6-pentafluorophenol

S-tert-butylmercapto-L-cysteine

Downstream raw materials:

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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