374114-86-0

Basic information

• Product Name: (3S,6R)-1-(o-Azidobenzoyl)-3-methyl-6-(3-indolylmethyl)-2,5-piperazinedione
• CAS NO: 374114-86-0
• Molecular Weight: 402.412
• Mol File: 374114-86-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (3S,6R)-1-(o-Azidobenzoyl)-3-methyl-6-(3-indolylmethyl)-2,5-piperazinedione(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,6R)-1-(o-Azidobenzoyl)-3-methyl-6-(3-indolylmethyl)-2,5-piperazinedione(374114-86-0)
• EPA Substance Registry System: (3S,6R)-1-(o-Azidobenzoyl)-3-methyl-6-(3-indolylmethyl)-2,5-piperazinedione(374114-86-0)

Safety Data

• Hazardous Substances Data: 374114-86-0(Hazardous Substances Data)

Upstream product

• 4299-70-1 D-Tryptophan methyl ester 
• 207349-42-6 (R)-2-((S)-2-tert-Butoxycarbonylamino-propionylamino)-3-(1H-indol-3-yl)-propionic acid methyl ester 
• 207349-41-5 Boc-D-Ala-D-Trp-OMe 
• 22839-21-0 cyclo-D-Trp-D-Ala 
• 17079-37-7 cyclo-D-Trp-L-Ala 
• 34897-85-3 o-azidobenzoyl chloride 

Relevant articles and documents

Regioselective N-acylation of 3-arylmethylpiperazine-2,5-diones: Short synthesis of (-)-glyantrypine and (-)-fumiquinazoline F

The folded conformation of the 3-arylmethyl substituent in 2,5-bis-O-trimethylsilyl-3,6-dihydropyrazines derived from the corresponding piperazine-2,5-diones, shields the N(1)-position allowing monoacylation at the neighbouring nitrogen atom. This regioselectivity was used to develop a four-step total synthesis of (-)-glyantrypine and (-)-fumiquinazoline F starting from D-tryptophan methyl ester.