L-Cysteine, N-[(1,1-dimethylethoxy)carbonyl]-, phenylmethyl ester

Base Information

• Chemical Name: L-Cysteine, N-[(1,1-dimethylethoxy)carbonyl]-, phenylmethyl ester
• CAS No.: 92278-78-9
• Molecular Formula: C15H21NO4S
• Molecular Weight: 311.402
• Mol file: 92278-78-9.mol

Synonyms:Boc-Cys-OBn;(R)-2-tert-Butoxycarbonylamino-3-mercapto-propionic acid benzyl ester;

Chemical Property of L-Cysteine, N-[(1,1-dimethylethoxy)carbonyl]-, phenylmethyl ester

Chemical Property:

• PSA: 103.43000
• LogP: 2.94380

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of L-Cysteine, N-[(1,1-dimethylethoxy)carbonyl]-, phenylmethyl ester

There total 9 articles about L-Cysteine, N-[(1,1-dimethylethoxy)carbonyl]-, phenylmethyl 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: 95.1%

(2R,2'R)-dibenzyl 3,3'-disulfanediylbis(2-((tert-butoxycarbonyl)amino)propanoate) (92278-77-8) → (R)-benzyl 2-((tert-butoxycarbonyl)amino)-3-mercaptopropanoate (92278-78-9)

Guidance literature:

(2R,2'R)-dibenzyl 3,3'-disulfanediylbis(2-((tert-butoxycarbonyl)amino)propanoate); With tributylphosphine; In tetrahydrofuran; at 20 ℃; for 0.5h;

With water; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1016/j.bmc.2019.05.005

Reference yield: 80.1%

N,N'-bis<(tert-butyloxy)carbonyl>cystine dibenzyl ester (92278-77-8) → N-cysteine benzyl ester (92278-78-9)

Guidance literature:

With sodium acetate; triphenylphosphine; In methanol; water; acetic acid; for 24h; Heating;

DOI:10.1021/jo00238a011

Reference yield:

[2-(2-tert-butoxycarbonylamino-2-chlorocarbonyl-ethyldisulfanyl)-1-chlorocarbonyl-ethyl]-carbamic acid tert-butyl ester → (R)-benzyl 2-((tert-butoxycarbonyl)amino)-3-mercaptopropanoate (92278-78-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 300 mg / DIEA / CH₂Cl₂ / 3 h / 25 °C

2: 94 percent / n-Bu₃P; H₂O / tetrahydrofuran / 2 h / 25 °C

With tributylphosphine; water; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol060993r

upstream raw materials:

N,N'-bis<(tert-butyloxy)carbonyl>cystine dibenzyl ester

N,N'-bis<(tert-butyloxy)carbonyl>cystine

benzyl bromide

(2R,2'R)-dibenzyl 3,3'-disulfanediylbis(2-((tert-butoxycarbonyl)amino)propanoate)

Downstream raw materials:

benzyl N-<(tert-butyloxy)carbonyl>-S-(2-hydroxypropyl)cysteine

L-cysteine benzyl ester

(2R)-(-)-benzyl 2-(tert-butoxycarbonylamino)-3-(2-hydroxyethylsulfanyl)propanoate