FMoc-N-Me-Cys(Trt)-OH

Base Information

• Chemical Name: FMoc-N-Me-Cys(Trt)-OH
• CAS No.: 944797-51-7
• Molecular Formula: C₃₈H₃₃NO₄S
• Molecular Weight: 599.75
• Hs Code.: 2930 90 16
• Mol file: 944797-51-7.mol

Synonyms:FMoc-N-Me-Cys(Trt)-OH;N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-N-methyl-S-(triphenylmethyl)-L-cysteine;(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-(tritylthio)propanoic acid

Chemical Property of FMoc-N-Me-Cys(Trt)-OH

Chemical Property:

• Melting Point: 234-239°C
• Boiling Point: 746.0±60.0 °C(Predicted)
• PKA: 3.72±0.10(Predicted)
• PSA: 92.14000
• Density: 1.260±0.06 g/cm3(Predicted)
• LogP: 8.04580
• Storage Temp.: 2-8°C

Purity/Quality:

≥98%,≥99%, ^*data from raw suppliers

Fmoc-N-Me-L-Cys(Trt)-OH ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Fmoc-N-Me-L-Cys(Trt)-OH (CAS# 944797-51-7) is an fmoc- and trityl-protected derivative of L-cysteine (C995000) used as a building block for peptides or peptide fragments, such as the solid-phase synthesis of Triostin A. Fmoc-N-Me-Cys(Trt)-OH is a Fmoc-protected derivative of N-methyl cysteine used as a building block to prepare peptide thioesters under acidic conditions. The residue attached to the amino group of N-methylcysteine can migrate to the cysteinyl thiol group, resulting in the formation of a peptide thioester. The introduction of this Fmoc-protected derivative is best achieved using HATU as a coupling reagent in the presence of DIPEA (N, N-Diisopropylethylamine). It can also be used to prepare Fmoc-N-Me-Cys(Trt)-OAllyl intermediate for the solid-phase synthesis of dithiol Triostin A.

Technology Process of FMoc-N-Me-Cys(Trt)-OH

There total 7 articles about FMoc-N-Me-Cys(Trt)-OH 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:

N-methyl-Cys(Trt) (166169-98-8) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → Fmoc-N-methyl-Cys(Trt) (1349807-46-0,944797-51-7)

Guidance literature:

With sodium carbonate;

DOI:10.1016/j.tetlet.2006.11.034

Reference yield:

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + C26H31NO2SSi → C38H33NO4S (1349807-46-0,944797-51-7)

Guidance literature:

In acetonitrile; at 0 ℃; for 1h;

DOI:10.1021/acs.orglett.0c02984

Reference yield:

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + C26H31NO2SSi → Fmoc-N-methyl-Cys(Trt) (1349807-46-0,944797-51-7)

Guidance literature:

In acetonitrile; at 0 ℃; for 1h;

DOI:10.1021/acs.orglett.0c02984

upstream raw materials:

N-methyl-Cys(Trt)

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

S-trityl-L-cysteine

(fluorenylmethoxy)carbonyl chloride

Refernces

• 1、 Sable, Ganesh A.,Lim, Dongyeol. "Solid-Phase Synthesis of Triostin A Using a Symmetrical Bis(diphenylmethyl) Linker System". . p. 7486 - 7494. Retrieved 2015/08/18.