L-Cysteine, 2-propenyl ester (9CI)

Base Information

• Chemical Name: L-Cysteine, 2-propenyl ester (9CI)
• CAS No.: 382591-09-5
• Molecular Formula: C₆H₁₁NO₂S
• Molecular Weight: 161.225
• Mol file: 382591-09-5.mol

Synonyms:L-Cysteine, 2-propenyl ester (9CI)

Chemical Property of L-Cysteine, 2-propenyl ester (9CI)

Chemical Property:

• PSA: 91.12000
• LogP: 0.67300

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of L-Cysteine, 2-propenyl ester (9CI)

There total 3 articles about L-Cysteine, 2-propenyl ester (9CI) 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: 82.0%

L-cystine-bis-allyl ester bis-(toluene-4-sulfonate) → cysteine allyl ester (382591-09-5)

Guidance literature:

With 1,4-dithio-L-threitol; triethylamine; In dichloromethane; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1039/d1sc05542a

Reference yield: 80.0%

(R)-allyl 2-(tert-butoxycarbonylamino)-3-mercaptopropanoate (149034-32-2) → cysteine allyl ester (382591-09-5)

Guidance literature:

With 20percent TFA; In dichloromethane; at 0 ℃; for 4h;

DOI:10.1021/ol016651x

Reference yield:

N-Boc-S-trityl-L-cysteine allyl ester → cysteine allyl ester (382591-09-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: AgNO₃; pyridine / methanol; ethyl acetate / 24 h / 23 °C

1.2: H₂S / ethyl acetate / 0.05 h / 23 °C

2.1: 80 percent / 20percent TFA / CH₂Cl₂ / 4 h / 0 °C

With pyridine; silver nitrate; In methanol; dichloromethane; ethyl acetate;

DOI:10.1021/ol016651x

upstream raw materials:

(R)-allyl 2-(tert-butoxycarbonylamino)-3-mercaptopropanoate

Refernces

• 1、 Genov, Miroslav,Moloney, Mark G.,Pretsch, Alexander,Pretsch, Dagmar,Zhang, Ruirui. "Mediation of metal chelation in cysteine-derived tetramate systems". . p. 16106 - 16122. Retrieved 2021/12/30.