N¹-(benzyloxycarbonyl)-N²-(tert-butyloxycarbonyl)-L-cystine ethyl tert-butyl diester

Base Information

• Chemical Name: N¹-(benzyloxycarbonyl)-N²-(tert-butyloxycarbonyl)-L-cystine ethyl tert-butyl diester
• CAS No.: 98303-75-4
• Molecular Formula: C₂₅H₃₈N₂O₈S₂
• Molecular Weight: 558.717

Synonyms:N¹-(benzyloxycarbonyl)-N²-(tert-butyloxycarbonyl)-L-cystine ethyl tert-butyl diester

Chemical Property of N¹-(benzyloxycarbonyl)-N²-(tert-butyloxycarbonyl)-L-cystine ethyl tert-butyl diester

Chemical Property:

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Technology Process of N¹-(benzyloxycarbonyl)-N²-(tert-butyloxycarbonyl)-L-cystine ethyl tert-butyl diester

There total 6 articles about N¹-(benzyloxycarbonyl)-N²-(tert-butyloxycarbonyl)-L-cystine ethyl tert-butyl diester 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: 55.0%

tert-butyl (2R)-2-{[(tert-butoxy)carbonyl]amino}-3-sulfanylpropanoate (98330-15-5) + C26H32N2O9S2 (98303-77-6) → N1-(benzyloxycarbonyl)-N2-(tert-butyloxycarbonyl)-L-cystine ethyl tert-butyl diester (98303-75-4)

Guidance literature:

With hexaethylphosphorous triamide; In benzene; for 5h;

DOI:10.1021/jo00222a026

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → N1-(benzyloxycarbonyl)-N2-(tert-butyloxycarbonyl)-L-cystine ethyl tert-butyl diester (98303-75-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / Et₃N / dimethylformamide / 5 h / Ambient temperature

2: 100 percent / 5percent AcOH, Zn / diethyl ether / 2 h / 0 °C

3: 55 percent / hexaethylphosphorus triamide / benzene / 5 h

With hexaethylphosphorous triamide; acetic acid; triethylamine; zinc; In diethyl ether; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jo00222a026

Reference yield:

tert-butyl (2R)-3-{[(2R)-3-(tert-butoxy)-2-{[(tert-butoxy)carbonyl]amino}-3-oxopropyl]disulfanyl}-2-{[(tert-butoxy)carbonyl]amino}propanoate (98303-76-5) → N1-(benzyloxycarbonyl)-N2-(tert-butyloxycarbonyl)-L-cystine ethyl tert-butyl diester (98303-75-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / 5percent AcOH, Zn / diethyl ether / 2 h / 0 °C

2: 55 percent / hexaethylphosphorus triamide / benzene / 5 h

With hexaethylphosphorous triamide; acetic acid; zinc; In diethyl ether; benzene;

DOI:10.1021/jo00222a026

upstream raw materials:

tert-butyl (2R)-2-{[(tert-butoxy)carbonyl]amino}-3-sulfanylpropanoate

C₂₆H₃₂N₂O₉S₂

di-tert-butyl dicarbonate

tert-butyl (2R)-3-{[(2R)-3-(tert-butoxy)-2-{[(tert-butoxy)carbonyl]amino}-3-oxopropyl]disulfanyl}-2-{[(tert-butoxy)carbonyl]amino}propanoate

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