Fmoc-D-Cys(Trt)-OH

Base Information

• Chemical Name: Fmoc-D-Cys(Trt)-OH
• CAS No.: 167015-11-4
• Molecular Formula: C₃₇H₃₁NO₄S
• Molecular Weight: 585.723
• Hs Code.: 2930 90 16
• European Community (EC) Number: 695-151-8
• DSSTox Substance ID: DTXSID90428234
• Nikkaji Number: J2.276.791G
• Wikidata: Q72479019
• Mol file: 167015-11-4.mol

Synonyms:Fmoc-D-Cys(Trt)-OH;167015-11-4;N-Fmoc-S-trityl-D-cysteine;Fmoc-S-trityl-D-cysteine;(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-tritylsulfanylpropanoic acid;D-Cysteine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-S-(triphenylmethyl)-;MFCD00151922;SCHEMBL3436122;DTXSID90428234;N-Alpha-(9-Fluorenylmethyloxycarbonyl)-S-Trityl-D-Cysteine;N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-S-(triphenylmethyl)-D-cysteine;(S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(tritylthio)propanoic acid;AKOS015837179;AKOS015896302;AM81676;CS-W011440;FD21244;HY-W010724;AC-29841;AS-19001;BP-23491;F0752;Fmoc-D-Cys(Trt)-OH, >=97.0% (HPLC);M03360;EN300-1178219;A810808;J-300087;Q-101677;N-(9H-Fluorene-9-ylmethoxycarbonyl)-S-trityl-D-cysteine;N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-S-trityl-D-cysteine;(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(tritylthio)propanoic acid;(2S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-[(triphenylmethyl)sulfanyl]propanoic acid;(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-tritylsulfanyl-propanoic acid;N-Fmoc-S-(triphenylmethyl)-D-cysteine

Chemical Property of Fmoc-D-Cys(Trt)-OH

Chemical Property:

• Melting Point: 172-176℃
• Boiling Point: 763.4 °C at 760 mmHg
• PKA: 3.70±0.10(Predicted)
• Flash Point: 415.5 °C
• PSA: 100.93000
• Density: 1.27 g/cm³
• LogP: 8.09450
• Storage Temp.: -15°C
• Solubility.: soluble in Tetrahydrofuran
• XLogP3: 8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 11
• Exact Mass: 585.19737964
• Heavy Atom Count: 43
• Complexity: 841

Purity/Quality:

≥98%,≥99%, ^*data from raw suppliers

N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-S-(triphenylmethyl)-D-cysteine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3)SCC(C(=O)O)NC(=O)OCC4C5=CC=CC=C5C6=CC=CC=C46
• Isomeric SMILES: C1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3)SC[C@H](C(=O)O)NC(=O)OCC4C5=CC=CC=C5C6=CC=CC=C46
• Uses: N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-S-(triphenylmethyl)-D-cysteine is a reagent in the identification and preparation of plasma-stable cyclic peptides as novel, potent C-X-C chemokine receptor type 4 antagonists with antitumor potential.

Technology Process of Fmoc-D-Cys(Trt)-OH

There total 9 articles about Fmoc-D-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: 100.0%

S-trityl-L-cysteine (2799-07-7) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → N-(9-fluorenylmethoxycarbonyl)-S-trityl-L-cysteine (103213-32-7,167015-11-4)

Guidance literature:

With sodium carbonate; In water; acetonitrile;

DOI:10.1021/acs.orglett.0c03850

Reference yield:

trityl chloride (76-83-5) → N-(9-fluorenylmethoxycarbonyl)-S-trityl-L-cysteine (103213-32-7,167015-11-4)

Guidance literature:

Multi-step reaction with 2 steps

1: N,N-dimethyl-formamide / 48 h / 20 °C

2: sodium carbonate / water; acetonitrile

With sodium carbonate; In water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/acs.orglett.0c03850

Reference yield:

L-Cys(trt)-OH dicyclohexylamine salt + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → N-(9-fluorenylmethoxycarbonyl)-S-trityl-L-cysteine (103213-32-7,167015-11-4)

Guidance literature:

L-Cys(trt)-OH dicyclohexylamine salt; N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide; With sodium carbonate; In water; acetonitrile; at 0 - 20 ℃; pH=8;

With potassium hydrogensulfate; In water; acetonitrile; pH=2 - 3;

DOI:10.1080/00397910802632563

upstream raw materials:

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

trityl chloride

N^α-fluoren-9-ylmethoxycarbonyl-L-cysteine

N,N'-bis[(9H-fluoren-9-ylmethoxy)carbonyl]-L-cystine

Refernces

• 1、 Castillo-Pazos, Durbis J.,Macmillan, Derek. "Investigation of Cysteine as an Activator of Side-Chain N→S Acyl Transfer and Tail-to-Side-Chain Cyclization". . p. 1923 - 1928. Retrieved 2017/09/13.
• 2、 Flemer, Stevenson. "A comprehensive one-pot synthesis of protected cysteine and selenocysteine SPPS derivatives". . p. 1257 - 1264. Retrieved 2015/04/14.