1135416-05-5

Basic information

• Product Name: methyl (2R,4R)-2-((1H-indol-3-yl)methyl)-4-(benzyloxycarbonylamino)-5-oxotetrahydrofuran-2-carboxylate
• CAS NO: 1135416-05-5
• Molecular Weight: 422.437
• Mol File: 1135416-05-5.mol

Chemical Properties

• CAS DataBase Reference: methyl (2R,4R)-2-((1H-indol-3-yl)methyl)-4-(benzyloxycarbonylamino)-5-oxotetrahydrofuran-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (2R,4R)-2-((1H-indol-3-yl)methyl)-4-(benzyloxycarbonylamino)-5-oxotetrahydrofuran-2-carboxylate(1135416-05-5)
• EPA Substance Registry System: methyl (2R,4R)-2-((1H-indol-3-yl)methyl)-4-(benzyloxycarbonylamino)-5-oxotetrahydrofuran-2-carboxylate(1135416-05-5)

Safety Data

• Hazardous Substances Data: 1135416-05-5(Hazardous Substances Data)

Upstream product

• 87438-91-3 ethyl 2-((1H-indol-3-yl)methyl)acrylate 
• 144-55-8 sodium hydrogencarbonate 

Relevant articles and documents

Scale-up of a chemo-biocatalytic route to (2 R,4 R)- and (2 S,4 S)-monatin

Monatin, a natural sweetener, refers to a collection of four isomers of 2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentanedioic acid. A chemo-biocatalytic approach to kilogram quantities of enantiopure 2S,4S-monatin and 2R,4R-monatin from indole is described. Key steps in the process include a (2 + 3) cycloaddition reaction followed by nickel-catalysed reduction to construct the monatin backbone, and a highly selective enzyme resolution of the 2S,4S- and 2R,4R-monatin diastereomeric pair to afford each enantiomer in 99% ee.

PRODUCTION OF MONATIN STEREOISOMERS

Methods and materials for the production of the high intensity sweetener, monatin, in stereoisomerically-pure or stereoisomerically-enriched form are disclosed. For example, methods using stereoisoselective hydrolysis and separation of a monatin-derived lactone ester are disclosed.