N,N'-bis(benzyloxycarbonyl)-L-cystine dibenzyl ester

Base Information

• Chemical Name: N,N'-bis(benzyloxycarbonyl)-L-cystine dibenzyl ester
• CAS No.: 64957-09-1
• Molecular Formula: C₃₆H₃₆N₂O₈S₂
• Molecular Weight: 688.822
• Mol file: 64957-09-1.mol

Synonyms:N,N'-bis(benzyloxycarbonyl)-L-cystine dibenzyl ester

Chemical Property of N,N'-bis(benzyloxycarbonyl)-L-cystine dibenzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of N,N'-bis(benzyloxycarbonyl)-L-cystine dibenzyl ester

There total 11 articles about N,N'-bis(benzyloxycarbonyl)-L-cystine dibenzyl 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: 87.0%

N,N'-bis(benzyloxycarbonyl)-L-cystine (6968-11-2) + benzyl alcohol (100-51-6,185532-71-2) → N,N'-bis(benzyloxycarbonyl)-L-cystine dibenzyl ester (64957-09-1)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; Ambient temperature;

DOI:10.1021/jo961043u

Reference yield: 76.0%

(S)-N-(benzyloxycarbonyl)-O-(p-toluenesulfonyl)serine benzyl ester (16938-05-9) → N,N'-bis(benzyloxycarbonyl)-L-cystine dibenzyl ester (64957-09-1)

Guidance literature:

With benzyltriethylammonium tetrathiomolybdate; In acetonitrile; at 28 ℃;

DOI:10.1016/S0040-4039(03)01222-X

Reference yield:

N-benzyloxycarbonyl-L-serine benzyl ester (21209-51-8) → N,N'-bis(benzyloxycarbonyl)-L-cystine dibenzyl ester (64957-09-1)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine

2: 76 percent / (BnNEt₃)2MoS₄ / acetonitrile / 28 °C

With benzyltriethylammonium tetrathiomolybdate; In pyridine; acetonitrile;

DOI:10.1016/S0040-4039(03)01222-X

upstream raw materials:

N,N'-bis(benzyloxycarbonyl)-L-cystine

toluene-4-sulfonic acid

benzyl alcohol

N.N'-bis-benzyloxycarbonyl-L-cystyl dichloride

Downstream raw materials:

(R)-2-Benzyloxycarbonylamino-3-ethoxysulfonyl-propionic acid benzyl ester

Z-Cys-OBzl

(R)-benzyl 2-(benzyloxycarbonylamino)-3-(chlorosulfonyl)propanoate

Refernces

• 1、 Bhat, Ramakrishna G.,Porhiel, Emmanuel,Saravanan, Vadivelu,Chandrasekaran, Srinivasan. "Utility of tetrathiomolybdate and tetraselenotungstate: Efficient synthesis of cystine, selenocystine, and their higher homologues". . p. 5251 - 5253. Retrieved 2007/10/03.
• 2、 Nakajima,Okawa. "STUDIES ON 2-AZIRIDINECARBOXYLIC ACID: X. SIMPLE STEREOSPECIFIC SYNTHESIS OF OPTICALLY ACTIVE CYSTINE AND THREO-3,3 prime -DIMETHYLCYSTINE.". . p. 1565 - 1566. Retrieved 2007/10/02.