108431-24-9

Basic information

• Product Name: (3S,5aS,10bR,11aS)-3-Benzyl-10b-hydroxy-2,3,6,10b,11,11a-hexahydro-5aH-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4-dione
• CAS NO: 108431-24-9
• Molecular Weight: 349.389
• Mol File: 108431-24-9.mol

Chemical Properties

• CAS DataBase Reference: (3S,5aS,10bR,11aS)-3-Benzyl-10b-hydroxy-2,3,6,10b,11,11a-hexahydro-5aH-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,5aS,10bR,11aS)-3-Benzyl-10b-hydroxy-2,3,6,10b,11,11a-hexahydro-5aH-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4-dione(108431-24-9)
• EPA Substance Registry System: (3S,5aS,10bR,11aS)-3-Benzyl-10b-hydroxy-2,3,6,10b,11,11a-hexahydro-5aH-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4-dione(108431-24-9)

Safety Data

• Hazardous Substances Data: 108431-24-9(Hazardous Substances Data)

Upstream product

• 7432-21-5 N-carbobenzyloxy-L-tryptophane 
• 643751-44-4 3a-phenylselanyl-2,3,3a,8a-tetrahydro-pyrrolo[2,3-b]indole-1,2,8-tricarboxylic acid 1-benzyl ester 8-tert-butyl ester 2-methyl ester 
• 643751-46-6 3a-hydroxy-2,3,3a,8a-tetrahydro-pyrrolo[2,3-b]indole-1,2,8-tricarboxylic acid 1-benzyl ester 8-tert-butyl ester 2-methyl ester 
• 643751-42-2 N-carbobenzyloxy-1-tert-butoxycarbonyl-L-tryptophan methyl ester 
• 643751-48-8 3a-hydroxy-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester 
• 643751-49-9 (2S,3aR,8aR)-3a-Hydroxy-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carboxylic acid methyl ester 
• 2717-76-2 (S)-N-benzyloxycarbonyl-L-tryptophan methyl ester 
• 82597-82-8 cyclo(L-tryptophyl-L-phenylalanyl) 

Relevant articles and documents

A rapid stereocontrolled synthesis of the 3a-hydroxy-pyrrolo[2,3-b]indole skeleton, a building block for 10b-hydroxypyrazino[1′,2′:1,5]pyrrolo[2,3-b]indole-1,4-diones

A study was performed on the rapid stereocontrolled synthesis of the 3a-hydroxy-pyrrolo-[2,3-b]indole skeleton. A two-step selenocyclisation-oxidative deselenation sequence was used for the synthesis. It is reported that many biologically active natural products are based on this structure, such as the sporidesmins and certain members of the brevianamide and okaramine families.

N.m.r. Assignments, Conformation, and Absolute Configuration of Ditryptophenaline and Model Dioxopiperazines

A detailed (1)H n.m.r. analysis was carried out in order to determine the solution conformations of ditryptophenaline (1) and the model dipeptide cyclo-(L-tryptophyl-L-phenylalanyl) (2), as well as two photo-oxidation products (3) and (4).In chloroform solution ditryptophenaline (1) exists in a conformation similar to the solid-state arrangement determined by X-ray crystallography, which involves a positive degree of folding (β) of the 2,5-dioxopiperazine (DOP) ring with the phenyl group in close proximity.The DOP ring of the dipeptide (2) has a negative degree of folding (β) in dimethyl sulphoxide solution with both substituents pseudo-axial.In this conformation the phenyl ring is forced away by the indole group that is situated over the DOP ring.The solution conformations of compounds (3) and (4) in dimethyl sulphoxide are similar to that of compound (1).The assignment of (13)C n.m.r. spectra of compounds (1)-(4) is reported as well as the absolute configuration of (1).