L-Cysteine, 2-methyl-N-[2-methyl-N-[2-methyl-N-[(phenylmethoxy)carbonyl]-S-(phen ylmethyl)-L-cysteinyl]-S-(phenylmethyl)-L-cysteinyl]-S-(phenylmethyl)-, methyl ester

Base Information

• Chemical Name: L-Cysteine, 2-methyl-N-[2-methyl-N-[2-methyl-N-[(phenylmethoxy)carbonyl]-S-(phen ylmethyl)-L-cysteinyl]-S-(phenylmethyl)-L-cysteinyl]-S-(phenylmethyl)-, methyl ester
• CAS No.: 143564-96-9
• Molecular Formula: C42H49N3O6S3
• Molecular Weight: 788.066
• Mol file: 143564-96-9.mol

Synonyms:

Chemical Property of L-Cysteine, 2-methyl-N-[2-methyl-N-[2-methyl-N-[(phenylmethoxy)carbonyl]-S-(phen ylmethyl)-L-cysteinyl]-S-(phenylmethyl)-L-cysteinyl]-S-(phenylmethyl)-, methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of L-Cysteine, 2-methyl-N-[2-methyl-N-[2-methyl-N-[(phenylmethoxy)carbonyl]-S-(phen ylmethyl)-L-cysteinyl]-S-(phenylmethyl)-L-cysteinyl]-S-(phenylmethyl)-, methyl ester

There total 3 articles about L-Cysteine, 2-methyl-N-[2-methyl-N-[2-methyl-N-[(phenylmethoxy)carbonyl]-S-(phen ylmethyl)-L-cysteinyl]-S-(phenylmethyl)-L-cysteinyl]-S-(phenylmethyl)-, methyl 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: 60.0%

Nα-benzyloxycarbonyl-S-benzyl-(R)-methylcysteine (143564-91-4) + (R)-2-((R)-2-Amino-3-benzylsulfanyl-2-methyl-propionylamino)-3-benzylsulfanyl-2-methyl-propionic acid methyl ester (745761-96-0) → (R)-2-[(R)-2-((R)-2-Benzyloxycarbonylamino-3-benzylsulfanyl-2-methyl-propionylamino)-3-benzylsulfanyl-2-methyl-propionylamino]-3-benzylsulfanyl-2-methyl-propionic acid methyl ester (143564-96-9)

Guidance literature:

With dmap; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; In dichloromethane; for 24h;

DOI:10.1021/jo00047a005

Reference yield:

(R)-2-Amino-3-benzylsulfanyl-2-methyl-propionic acid methyl ester; hydrochloride (143564-93-6) → (R)-2-[(R)-2-((R)-2-Benzyloxycarbonylamino-3-benzylsulfanyl-2-methyl-propionylamino)-3-benzylsulfanyl-2-methyl-propionylamino]-3-benzylsulfanyl-2-methyl-propionic acid methyl ester (143564-96-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / bromotris(pyrrolidino)phosphonium hexafluorophosphate, i-Pr₂NEt, DMAP / CH₂Cl₂ / 4 h

2: 100 percent / HBr, HOAc

3: 60 percent / bromotris(pyrrolidino)phosphonium hexafluorophosphate, i-Pr₂NEt, DMAP / CH₂Cl₂ / 24 h

With dmap; hydrogen bromide; acetic acid; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; In dichloromethane;

DOI:10.1021/jo00047a005

Reference yield:

(R)-2-((R)-2-Benzyloxycarbonylamino-3-benzylsulfanyl-2-methyl-propionylamino)-3-benzylsulfanyl-2-methyl-propionic acid methyl ester (143564-94-7) → (R)-2-[(R)-2-((R)-2-Benzyloxycarbonylamino-3-benzylsulfanyl-2-methyl-propionylamino)-3-benzylsulfanyl-2-methyl-propionylamino]-3-benzylsulfanyl-2-methyl-propionic acid methyl ester (143564-96-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / HBr, HOAc

2: 60 percent / bromotris(pyrrolidino)phosphonium hexafluorophosphate, i-Pr₂NEt, DMAP / CH₂Cl₂ / 24 h

With dmap; hydrogen bromide; acetic acid; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; In dichloromethane;

DOI:10.1021/jo00047a005

upstream raw materials:

N^α-benzyloxycarbonyl-S-benzyl-(R)-methylcysteine

(R)-2-((R)-2-Amino-3-benzylsulfanyl-2-methyl-propionylamino)-3-benzylsulfanyl-2-methyl-propionic acid methyl ester

(R)-2-Amino-3-benzylsulfanyl-2-methyl-propionic acid methyl ester; hydrochloride

(R)-2-((R)-2-Benzyloxycarbonylamino-3-benzylsulfanyl-2-methyl-propionylamino)-3-benzylsulfanyl-2-methyl-propionic acid methyl ester

Downstream raw materials:

(R)-3-Benzylsulfanyl-N-[(R)-2-benzylsulfanyl-1-(2-benzylsulfanyl-ethylcarbamoyl)-1-methyl-ethyl]-2-((R)-3-benzylsulfanyl-2-isobutyrylamino-2-methyl-propionylamino)-2-methyl-propionamide

(R)-3-Benzylsulfanyl-2-[(R)-3-benzylsulfanyl-2-((R)-3-benzylsulfanyl-2-isobutyrylamino-2-methyl-propionylamino)-2-methyl-propionylamino]-2-methyl-propionic acid methyl ester

(R)-3-Benzylsulfanyl-2-[(R)-3-benzylsulfanyl-2-((R)-3-benzylsulfanyl-2-isobutyrylamino-2-methyl-propionylamino)-2-methyl-propionylamino]-2-methyl-propionic acid

C₆H₅CH₂CH₂CO-(R)-MeCys(Bn)-(R)-MeCys(Bn)-(R)-MeCys(Bn)-Thr(Bn)-NHCH₃