6686-03-9

Basic information

• Product Name: (S)-benzyl 2-(((S)-3-(1H-indol-3-yl)-1-methoxy-1-oxopropan-2-yl)carbamoyl)pyrrolidine-1-carboxylate
• Synonyms: (S)-benzyl 2-(((S)-3-(1H-indol-3-yl)-1-methoxy-1-oxopropan-2-yl)carbamoyl)pyrrolidine-1-carboxylate
• CAS NO: 6686-03-9
• Molecular Weight: 449.506
• Mol File: 6686-03-9.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (S)-benzyl 2-(((S)-3-(1H-indol-3-yl)-1-methoxy-1-oxopropan-2-yl)carbamoyl)pyrrolidine-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-benzyl 2-(((S)-3-(1H-indol-3-yl)-1-methoxy-1-oxopropan-2-yl)carbamoyl)pyrrolidine-1-carboxylate(6686-03-9)
• EPA Substance Registry System: (S)-benzyl 2-(((S)-3-(1H-indol-3-yl)-1-methoxy-1-oxopropan-2-yl)carbamoyl)pyrrolidine-1-carboxylate(6686-03-9)

Safety Data

• Hazardous Substances Data: 6686-03-9(Hazardous Substances Data)

Upstream product

• 7524-52-9 (S)-tryptophan methyl ester hydrochloride 
• 111491-98-6 (2S)-2-Acetyl-N-(benzyloxycarbonyl)pyrrolidine 
• 1059596-61-0 N-Cbz-L-proline p-tolylthiol ester 
• 1148-11-4 N-Benzyloxycarbonyl-L-proline 
• 147-85-3 L-proline 
• 501-53-1 benzyl chloroformate 
• 105414-01-5 Cbz-L-Pro-OCO₂-i-Bu 

Relevant articles and documents

Gold-catalyzed direct alkynylation of tryptophan in peptides using TIPS-EBX

The selective functionalization of peptides containing only natural amino acids is important for the modification of biomolecules. In particular, the installation of an alkyne as a useful handle for bioconjugation is highly attractive, but the use of a carbon linker is usually required. Herein, we report the gold-catalyzed direct alkynylation of tryptophan in peptides using the hypervalent iodine reagent TIPS-EBX (1-[(triisopropylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one). The reaction proceeded in 50-78% yield under mild conditions and could be applied to peptides containing other nucleophilic and aromatic amino acids, such as serine, phenylalanine or tyrosine.

Solvent-free asymmetric aldol reaction organocatalyzed by (S)-proline-containing thiodipeptides under ball-milling conditions

An efficient, solvent-free ball-milling protocol for the asymmetric aldol reaction between cyclohexanone and cyclopentanone with various aromatic aldehydes using a novel series of (S)-proline-containing dipeptides and thiodipeptides 1a-f as organocatalysts is reported. In general, (S)-proline-containing thiodipeptides proved to be better organocatalysts relative to their analogous amides. In particular, thiodipeptide (S,S)-1d catalyzed the stereoselective formation of the expected aldol products with excellent diastereo- and enantioselectivity (up to 98:2 anti/syn dr and up to 96% ee). This observation may be ascribed to the increased N-H acidity of the thioamide segment that leads to stronger H-bonding interaction with the aldehyde carbonyl at the transition state and thus higher stereoinduction. Furthermore, thiodipeptide 1f proved to be an efficient organocatalyst for the aldol reaction of acetone with isatin and isatin derivatives (ee 56-86%).