Fmoc-S-benzyl-D-cysteine

Base Information

• Chemical Name: Fmoc-S-benzyl-D-cysteine
• CAS No.: 252049-18-6
• Molecular Formula: C₂₅H₂₃NO₄S
• Molecular Weight: 433.528
• DSSTox Substance ID: DTXSID30544407
• Wikidata: Q82421508
• Mol file: 252049-18-6.mol

Synonyms:Fmoc-S-benzyl-D-cysteine;252049-18-6;Fmoc-D-Cys(Bzl)-OH;(2S)-3-benzylsulfanyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(benzylthio)propanoic acid;Fmoc-(S)-benzyl-L-Cys;Fmoc-Cys(Bzl)-OH;DTXSID30544407;D-Cysteine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-S-(phenylmethyl)-;AKOS015837442;AKOS015888721;(2S)-3-(benzylsulfanyl)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}propanoic acid;AS-72157;Fmoc-D-Cys(Bzl)-OH, >=98.0% (HPLC);J-015870;S-Benzyl-N-{[(9H-fluoren-9-yl)methoxy]carbonyl}-D-cysteine;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(benzylthio)propanoicacid;(S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(benzylthio)propanoic acid

Chemical Property of Fmoc-S-benzyl-D-cysteine

Chemical Property:

• Boiling Point: 663.2±55.0 °C(Predicted)
• PKA: 3.47±0.10(Predicted)
• PSA: 100.93000
• Density: 1.298±0.06 g/cm3(Predicted)
• LogP: 5.30260
• Storage Temp.: 2-8°C
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 433.13477939
• Heavy Atom Count: 31
• Complexity: 586

Purity/Quality:

99.3% ^*data from raw suppliers

Fmoc-S-benzyl-D-cysteine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CSCC(C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
• Isomeric SMILES: C1=CC=C(C=C1)CSC[C@H](C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24

Technology Process of Fmoc-S-benzyl-D-cysteine

There total 7 articles about Fmoc-S-benzyl-D-cysteine 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: 99.0%

S-benzyl-L-cysteine (3054-01-1,25988-62-9) + (9-fluorenyl)methyl pentafluorophenyl carbonate (88744-04-1) → Nα-Fmoc-S-benzylcysteine (53298-33-2,252049-18-6)

Guidance literature:

With sodium hydrogencarbonate; In water; acetone; Ambient temperature;

Reference yield: 90.0%

S-benzyl-L-cysteine (3054-01-1,25988-62-9) → Nα-Fmoc-S-benzylcysteine (53298-33-2,252049-18-6)

Guidance literature:

DOI:10.1055/s-1983-30327

Reference yield: 29.0%

S-benzyl-L-cysteine (3054-01-1,25988-62-9) + (fluorenylmethoxy)carbonyl chloride (28920-43-6) → Nα-Fmoc-S-benzylcysteine (53298-33-2,252049-18-6)

Guidance literature:

S-benzyl-L-cysteine; With chloro-trimethyl-silane; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20 ℃; for 0.5h;

(fluorenylmethoxy)carbonyl chloride; In acetonitrile; at 0 ℃; for 0.5h;

DOI:10.1021/acs.jmedchem.9b02119

upstream raw materials:

S-benzyl-L-cysteine

(9-fluorenyl)methyl pentafluorophenyl carbonate

benzyl bromide

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

Downstream raw materials:

Fmoc-Cys(Bzl)-O^tBu

N-(((9H-fluoren-9-yl)methoxy)carbonyl)-S-((3-nitropyridin-2-yl)thio)-L-cysteine

H-Gly-L-Cys-Phe-NH₂

C₃₅H₃₈N₂O₉S