58885-35-1

Basic information

• Product Name: L-Cysteine, S-(triphenylmethyl)-, methyl ester
• Synonyms: H2N-L-Cys(STrit)-OMe;L-(S)-Tr-cysteine methyl ester;methyl 2-amino-3-(tritylthio)propanoate;L-(S)-tritylcysteine methyl ester;H-Cys(Trt)-OMe;2-amino-3-(tritylsulfanyl)propionic acid methyl ester
• CAS NO: 58885-35-1
• Molecular Formula: C23H23NO2S
• Molecular Weight: 377.507
• Mol File: 58885-35-1.mol
• Article Data: 22

Chemical Properties

• Melting Point: 76 °C
• Boiling Point: 498.5±45.0 °C(Predicted)
• Density: 1.178±0.06 g/cm3(Predicted)
• CAS DataBase Reference: L-Cysteine, S-(triphenylmethyl)-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-Cysteine, S-(triphenylmethyl)-, methyl ester(58885-35-1)
• EPA Substance Registry System: L-Cysteine, S-(triphenylmethyl)-, methyl ester(58885-35-1)

Safety Data

• Hazardous Substances Data: 58885-35-1(Hazardous Substances Data)

Upstream product

• 21947-98-8 N-tert-butyloxycarbonyl-S-trityl-L-cysteine 
• 76-83-5 trityl chloride 
• 103213-32-7 N-(9-fluorenylmethoxycarbonyl)-S-trityl-L-cysteine 
• 76-84-6 triphenylmethyl alcohol 
• 18598-63-5 L-cysteine methyl ester hydrochloride 
• 67-56-1 methanol 
• 2799-07-7 S-trityl-L-cysteine 
• 245088-56-6 Fmoc-Cys(Trt)-OMe 
• 158022-23-2 (R)-methyl 2-((tert-butoxycarbonyl)amino)-3-(tritylthio)propanoate 
• 77-76-9 2,2-dimethoxy-propane 

Downstream Products

• 309264-63-9 N-dihydrocinnamoyl-S-trityl-L-cysteine methyl ester 
• 647026-17-3 (R)-2-(4-Bromo-butyrylamino)-3-tritylsulfanyl-propionic acid methyl ester 
• 647026-18-4 (R)-methyl 2-(5-bromopentanamido)-3-(tritylthio)propanoate 
• 647026-19-5 (R)-2-(6-Bromo-hexanoylamino)-3-tritylsulfanyl-propionic acid methyl ester 
• 68869-57-8 C₃₃H₄₀N₂O₅S 
• 139924-70-2 Boc-Ala-Cys(Trt)-OMe 
• 68869-58-9 N-(tert-butyloxycarbonyl)phenylalanyl-S-tritylcysteine methyl ester 
• 676270-53-4 Boc-Gly-L-Cys(STrit)-OMe 
• 647026-16-2 (R)-2-(3-Bromo-propionylamino)-3-tritylsulfanyl-propionic acid methyl ester 
• 647026-15-1 (R)-2-(2-Bromo-acetylamino)-3-tritylsulfanyl-propionic acid methyl ester 
• 357636-26-1 (2R)-2-(3-methyl-but-2-enoylamino)-3-tritylsulfanyl-propionic acid methyl ester 
• 309264-61-7 N-(4-nitrobenzoyl)-S-trityl-L-cysteine methyl ester 
• 309264-62-8 N-(4-methoxybenzoyl)-S-trityl-L-cysteine methyl ester 

Relevant articles and documents

Oxidative peptide bond formation of glycine-amino acid using 2-(aminomethyl)malononitrile as a glycine unit

Amide linkage of glycine-amino acid was synthesized by coupling of substituted 2-(aminomethyl)malononitrile as a C-terminal glycine unit and N-terminal amine using CsOAc and O2in an aqueous solution. This is a coupling reagent-free and catalyst-free peptide synthesisviaoxidative amide bond formation. Various tripeptides and tetrapeptides were synthesized efficiently and the sulfide moiety is inert even under an oxygen atmosphere.

TUBULYSIN DERIVATIVES AND METHODS FOR PREPARING THE SAME

The invention relates to novel means and methods for the synthesis of tubulysin and derivatives thereof, which find their use e.g. as cytotoxic agents in targeted drug delivery. Provided is a method for preparing a tubulysin derivative, comprising reacting compounds A, B and C in a 3- component Passerini reaction, wherein compound A is a carboxylic acid according to the general formula (A); wherein compound B is an aldehyde according to the general formula (B); and wherein compound C is an isocyanide according to the general formula (C).

Tubulysin Synthesis Featuring Stereoselective Catalysis and Highly Convergent Multicomponent Assembly

A concise and modular total synthesis of the highly potent N14-desacetoxytubulysin H (1) has been accomplished in 18 steps in an overall yield of up to 30percent. Our work highlights the complexity-augmenting and route-shortening power of diastereoselective multicomponent reaction (MCR) as well as the role of bulky ligands to perfectly control both the regioselective and diastereoselective synthesis of tubuphenylalanine in just two steps. The total synthesis not only provides an operationally simple and step economy but will also stimulate major advances in the development of new tubulysin analogues.