L-Cysteine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-, methyl ester

Base Information

• Chemical Name: L-Cysteine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-, methyl ester
• CAS No.: 233266-69-8
• Molecular Formula: C19H19NO4S
• Molecular Weight: 357.43
• Mol file: 233266-69-8.mol

Synonyms:fluorenylmethyloxycarbonylcysteine methyl ester;Nα-9-fluorenylmethoxycarbonyl-L-cysteine methyl ester;2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-mercaptopropionic acid methyl ester;Fmoc-Cys-OCH3;(2R)-N-(9H-fluorenylmethoxycarbonyl)cysteine methyl ester;

Chemical Property of L-Cysteine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-, methyl ester

Chemical Property:

• Boiling Point: 548.9±50.0 °C(Predicted)
• PKA: 9.24±0.10(Predicted)
• PSA: 103.43000
• Density: 1.266±0.06 g/cm3(Predicted)
• LogP: 3.38740

Purity/Quality:

99% ^*data from raw suppliers

N-Fmoc-L-cysteine methyl ester 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of L-Cysteine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-, methyl ester

There total 13 articles about L-Cysteine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-, 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: 98.0%

Fmoc-Cys(Trt)-OMe (245088-56-6) → 2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-mercaptopropionic acid methyl ester (233266-69-8)

Guidance literature:

With chlorotriisopropylsilane; trifluoroacetic acid; In dichloromethane; at 20 ℃; for 4h;

Reference yield: 97.0%

methanol (67-56-1) + Nα-fluoren-9-ylmethoxycarbonyl-L-cysteine (135248-89-4) → 2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-mercaptopropionic acid methyl ester (233266-69-8)

Guidance literature:

With hydrogenchloride; In water;

DOI:10.1021/ol302592v

Reference yield: 97.0%

C38H31NO4S → 2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-mercaptopropionic acid methyl ester (233266-69-8)

Guidance literature:

With chlorotriisopropylsilane; trifluoroacetic acid; In dichloromethane; ethylene glycol; at 20 ℃; for 0.5h;

DOI:10.1021/acs.joc.9b02809

upstream raw materials:

tert-butyl fluoroformate

N^α-9-fluorenylmethyloxycarbonyl-S-allyloxycarbonylaminomethyl-L-cysteine methyl ester

di-tert-butyl dicarbonate

N^α-9-fluorenylmethoxycarbonyl-S-[N-[2,3,5,6-tetrafluoro-4-(N'-piperidino)phenyl]-N-(allyloxycarbonyl)aminomethyl]cysteine methyl ester

Downstream raw materials:

methyl (2S)-N-tritylaziridine-2-carboxylate

N-CBz,N-Fmoc-L-cysteine disulfide ethyl(N-CBz), methyl(N-Fmoc) diester

YIIKGVFWDPAC-OCH₃

H-Gly-Phe-L-Cys-OCH₃

Refernces

• 1、 Silva Nigenda, Ezequiel,Postma, Tobias M.,Hezwani, Mohammed,Pirvan, Alin,Gannon, Susan,Smith, Carol-Anne,Riehle, Mathis,Liskamp, Rob M. J.. "Synthesis and cellular penetration properties of new phosphonium based cationic amphiphilic peptides". . p. 982 - 987. Retrieved 2018.
• 2、 -. "LIQUID COMPOSITIONS COMPRISING A LEVODOPA AMINO ACID CONJUGATE AND USES THEREOF". . . Retrieved 2021/03/13.
• 3、 Soley, Jacob,Taylor, Scott D.. "Mild, Rapid, and Chemoselective Procedure for the Introduction of the 9-Phenyl-9-fluorenyl Protecting Group into Amines, Acids, Alcohols, Sulfonamides, Amides, and Thiols". . . Retrieved 2020/02/04.