{(R)-2-Benzyloxycarbonylamino-3-[(R)-2-benzyloxycarbonylamino-2-(tert-butoxycarbonylmethyl-carbamoyl)-ethyldisulfanyl]-propionylamino}-acetic acid tert-butyl ester

Base Information

• Chemical Name: {(R)-2-Benzyloxycarbonylamino-3-[(R)-2-benzyloxycarbonylamino-2-(tert-butoxycarbonylmethyl-carbamoyl)-ethyldisulfanyl]-propionylamino}-acetic acid tert-butyl ester
• CAS No.: 191151-92-5
• Molecular Formula: C₃₄H₄₆N₄O₁₀S₂
• Molecular Weight: 734.892
• Mol file: 191151-92-5.mol

Synonyms:{(R)-2-Benzyloxycarbonylamino-3-[(R)-2-benzyloxycarbonylamino-2-(tert-butoxycarbonylmethyl-carbamoyl)-ethyldisulfanyl]-propionylamino}-acetic acid tert-butyl ester

Chemical Property of {(R)-2-Benzyloxycarbonylamino-3-[(R)-2-benzyloxycarbonylamino-2-(tert-butoxycarbonylmethyl-carbamoyl)-ethyldisulfanyl]-propionylamino}-acetic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(R)-2-Benzyloxycarbonylamino-3-[(R)-2-benzyloxycarbonylamino-2-(tert-butoxycarbonylmethyl-carbamoyl)-ethyldisulfanyl]-propionylamino}-acetic acid tert-butyl ester

There total 4 articles about {(R)-2-Benzyloxycarbonylamino-3-[(R)-2-benzyloxycarbonylamino-2-(tert-butoxycarbonylmethyl-carbamoyl)-ethyldisulfanyl]-propionylamino}-acetic acid tert-butyl 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: 86.0%

Glycine tert-butyl ester (6456-74-2) + N,N'-bis[(phenylmethoxy)carbonyl]-L-cystine 1,1'-dimethyl ester (3693-95-6) → {(R)-2-Benzyloxycarbonylamino-3-[(R)-2-benzyloxycarbonylamino-2-(tert-butoxycarbonylmethyl-carbamoyl)-ethyldisulfanyl]-propionylamino}-acetic acid tert-butyl ester (191151-92-5)

Guidance literature:

In tetrahydrofuran; at 25 ℃; for 288h;

Reference yield: 60.0%

N,N'-bis(benzyloxycarbonyl)-L-cystine (6968-11-2) + glycine tert-butyl ester hydrochloride (27532-96-3) → {(R)-2-Benzyloxycarbonylamino-3-[(R)-2-benzyloxycarbonylamino-2-(tert-butoxycarbonylmethyl-carbamoyl)-ethyldisulfanyl]-propionylamino}-acetic acid tert-butyl ester (191151-92-5)

Guidance literature:

With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20 ℃;

DOI:10.1139/V07-011

Reference yield:

L-cystine (56-89-3) → {(R)-2-Benzyloxycarbonylamino-3-[(R)-2-benzyloxycarbonylamino-2-(tert-butoxycarbonylmethyl-carbamoyl)-ethyldisulfanyl]-propionylamino}-acetic acid tert-butyl ester (191151-92-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / NaHCO₃ / H₂O / 20 °C

2: 60 percent / DIEA; TBTU / acetonitrile / 20 °C

With sodium hydrogencarbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In water; acetonitrile;

DOI:10.1139/V07-011

upstream raw materials:

Glycine tert-butyl ester

N,N'-bis[(phenylmethoxy)carbonyl]-L-cystine 1,1'-dimethyl ester

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

glycine tert-butyl ester hydrochloride

Downstream raw materials:

N-benzyloxycarbonyl-L-cysteinylglycine tert-butyl ester

N-benzyloxycarbonyl-S-(p-nitrophenyloxycarbonyl)-L-cysteinylglycine

N-benzyloxycarbonyl-S-(p-nitrophenyloxycarbonyl)-L-cysteinylglycine tert-butyl ester