1353844-73-1

Basic information

• Product Name: (1R,3S)-methyl 1-(3,4-dibenzoyloxyphenyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate
• Synonyms: (1R,3S)-methyl 1-(3,4-dibenzoyloxyphenyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate
• CAS NO: 1353844-73-1
• Molecular Weight: 546.579
• Mol File: 1353844-73-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (1R,3S)-methyl 1-(3,4-dibenzoyloxyphenyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,3S)-methyl 1-(3,4-dibenzoyloxyphenyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate(1353844-73-1)
• EPA Substance Registry System: (1R,3S)-methyl 1-(3,4-dibenzoyloxyphenyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate(1353844-73-1)

Safety Data

• Hazardous Substances Data: 1353844-73-1(Hazardous Substances Data)

Upstream product

• 4299-70-1 L-tryptophan methyl ester 
• 54917-85-0 3,4-dibenzoyloxybenzaldehyde 
• 7524-52-9 (S)-tryptophan methyl ester hydrochloride 

Relevant articles and documents

A general strategy for the highly stereoselective synthesis of HR22C16-like mitotic kinesin Eg5 inhibitors from both l- and d-tryptophans

An efficient and general strategy for the highly stereoselective synthesis of HR22C16-like mitotic kinesin Eg5 inhibitors 1 from both l- and d-tryptophan methyl ester hydrohalides is described. (1R,3S)-trans-1,3-Disubstituted 1,2,3,4-tetrahydro-β-carbolines (1R,3S)-trans-2 could be obtained in high yields and with high stereoselectivities from the Pictet-Spengler reaction of l-tryptophan methyl ester hydrohalide with some 3-acyloxyl benzaldehydes via a CIAT (crystal induced asymmetric transformation) process, whereas (1R,3R)-cis-1,3-disubstituted 1,2,3,4-tetrahydro-β-carbolines (1R,3R)-cis-2 could also be obtained in high yields and with high stereoselectivities from a Pictet-Spengler reaction of d-tryptophan methyl ester hydrohalide with some other 3-acyloxyl benzaldehydes via a CIAT process. Both compounds (1R,3S)-trans-2 and (1R,3R)-cis-2 were efficiently converted into HR22C16-like mitotic kinesin Eg5 inhibitors 1 by the same one-pot procedure through tandem reactions. A total of eighteen target compounds 1 were obtained from six intermediate compounds 2 in 87-95% yields.