136057-11-9

Basic information

• Product Name: dimethyl (2S,3aR,8aS)-8-benzenesulphonyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-1,2-dicarboxylate
• Synonyms: dimethyl (2S,3aR,8aS)-8-benzenesulphonyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-1,2-dicarboxylate
• CAS NO: 136057-11-9
• Molecular Weight: 416.455
• Mol File: 136057-11-9.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: dimethyl (2S,3aR,8aS)-8-benzenesulphonyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-1,2-dicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: dimethyl (2S,3aR,8aS)-8-benzenesulphonyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-1,2-dicarboxylate(136057-11-9)
• EPA Substance Registry System: dimethyl (2S,3aR,8aS)-8-benzenesulphonyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-1,2-dicarboxylate(136057-11-9)

Safety Data

• Hazardous Substances Data: 136057-11-9(Hazardous Substances Data)

Upstream product

• 79465-82-0 L-(2β,3aα,8aα)-1,2,3,3a,8,8a-hexahydro-1,2-dimethoxycarbonylpyrrolo<2,3-b>indole 
• 7524-52-9 (S)-tryptophan methyl ester hydrochloride 
• 66377-68-2 N-(methoxycarbonyl)-L-tryptophan methyl ester 
• 79631-04-2 N_α-methoxycarbonyl-D-tryptophan methyl ester 
• 151414-50-5 (+)-(2S,3aS,8aS)-3a-Bromo-1,2-bis(methoxycarbonyl)-8-(phenylsulfonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole 
• 98-09-9 benzenesulfonyl chloride 

Downstream Products

• 143100-48-5 (S)-3-(1-Benzenesulfonyl-1H-indol-3-yl)-2-methoxycarbonylamino-2-methyl-propionic acid methyl ester 
• 1333120-78-7 C₂₃H₂₆N₂O₆S 
• 1356557-83-9 C₄₅H₅₃N₅O₁₁S 
• 1356557-84-0 C₃₄H₃₄N₄O₁₀S 
• 1356557-85-1 C₄₈H₅₉N₅O₁₁S 
• 1333120-83-4 C₃₆H₄₇N₃O₉S 
• 143100-49-6 (R)-2-(1-Benzenesulfonyl-1H-indol-3-ylmethyl)-2-methoxycarbonylamino-succinic acid dimethyl ester 
• 141870-94-2 (2S,3aR,8aS)-8-Benzenesulfonyl-2-isobutoxycarbonyloxycarbonyl-2-methyl-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1-carboxylic acid methyl ester 
• 145682-65-1 erythro-β-Phenyl-L-tryptophan hydrochloride 
• 141870-93-1 (+)-(2S,3aR,8aS)-1-(Methoxycarbonyl)-2-methyl-8-(phenylsulfonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-2-carboxylic acid 
• 145814-46-6 dimethyl (2R,3aR,8aS)-2-(hydroxymethyl)-8-(phenylsulfonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate 
• 73804-81-6 α(S)-(fluoromethyl)tryptophan 
• 146138-86-5 (αS)-1-benzenesulfonyl-α-(1-methylethyl)-N_b-methoxycarbonyltryptophan methyl ester 
• 146138-85-4 (αS)-1-benzenesulfonyl-α-ethyl-N_b-methoxycarbonyltryptophan methyl ester 

Relevant articles and documents

Orthogonal protecting groups in the synthesis of tryptophanyl- hexahydropyrroloindoles

The synthesis of various polycyclic systems containing aC 3a-Ni bond between a hexahydropyrrolo[2,3-b]indole and an indole tryptophan is described here. A series of experiments were performed to determine the best combination of five orthogonal protecting groups and the best reaction conditions for formation of said bond, which is a common feature among many recently discovered marine natural products.

Concise total synthesis of (-)-calycanthine, (+)-chimonanthine, and (+)-folicanthine

Conjoined twins: An efficient and convergent strategy for the synthesis of the dimeric hexahydropyrroloindole alkaloids, (+)-chimonanthine, (+)-folicanthine, and (-)-calycanthine, is described. The simultaneous formation of the vicinal quaternary stereocenters by using a reductive dimerization reaction provides an access to the optically active key intermediate on a gram scale. (Chemical Equation Presented).

ENANTIOSPECIFIC SYNTHESIS OF AMINO ACIDS: PREPARATION OF (R)- AND (S)-α-METHYLASPARTIC ACID FROM (S)-TRYPTOPHAN

The enantiospecific synthesis of both antipodes of α-methylaspartic acid from (S)-tryptophan is described with the key steps being alkylation of the hexahydropyrroloindole 4, oxidative degradation of indoles and, for the preparation of the (R)-isomer, Barton reductive decarboxylation.