914649-70-0

Basic information

• Product Name: (2S,5S)-2-benzyloxymethyl-5-[5-{(5S,7S)-1,6-dioxa-spiro[4.5]dec-7-yl}-pentanoyl]-2,5-dihydro-pyrrole-1-carboxylic acid benzyl ester
• Synonyms: (2S,5S)-2-benzyloxymethyl-5-[5-{(5S,7S)-1,6-dioxa-spiro[4.5]dec-7-yl}-pentanoyl]-2,5-dihydro-pyrrole-1-carboxylic acid benzyl ester
• CAS NO: 914649-70-0
• Molecular Weight: 547.692
• Mol File: 914649-70-0.mol

Chemical Properties

• CAS DataBase Reference: (2S,5S)-2-benzyloxymethyl-5-[5-{(5S,7S)-1,6-dioxa-spiro[4.5]dec-7-yl}-pentanoyl]-2,5-dihydro-pyrrole-1-carboxylic acid benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,5S)-2-benzyloxymethyl-5-[5-{(5S,7S)-1,6-dioxa-spiro[4.5]dec-7-yl}-pentanoyl]-2,5-dihydro-pyrrole-1-carboxylic acid benzyl ester(914649-70-0)
• EPA Substance Registry System: (2S,5S)-2-benzyloxymethyl-5-[5-{(5S,7S)-1,6-dioxa-spiro[4.5]dec-7-yl}-pentanoyl]-2,5-dihydro-pyrrole-1-carboxylic acid benzyl ester(914649-70-0)

Safety Data

• Hazardous Substances Data: 914649-70-0(Hazardous Substances Data)

Upstream product

• 660391-02-6 (2S,5S)-5-benzyloxymethyl-5-(methoxy-methyl-carbamoyl)-2,5-dihydro-pyrrole-1-carboxylic acid benzyl ester 
• 660391-17-3 (2S,5S)-(5-benzyloxymethyl-2,5-dihydro-1H-pyrrol-2-yl)-methanol 
• 660390-94-3 [4S,3(1S)]-3-(1-hydroxymethyl-allyl)-4-vinyl-oxazolidin-2-one 
• 660390-99-8 (3S,6aS)-1,2-dehydro-3-benzyloxymethyl-5-oxapyrrolizidin-4-one 
• 660391-09-3 [4S,3(1S)]-3-[1-benzyloxymethyl-allyl]-4-vinyl-oxazolidin-2-one 
• 660391-00-4 (2S,5S)-2-benzyloxymethyl-5-hydroxymethyl-2,5-dihydro-pyrrole-1-carboxylic acid benzyl ester 
• 660391-10-6 (2S,5S)-5-benzyloxymethyl-2,5-dihydro-pyrrole-1,2-dicarboxylic acid 1-benzyl ester 
• 914650-59-2 (5S,7R)-7-(4-bromo-butyl)-1,6-dioxaspiro[4.5]decane 

Downstream Products

• 914649-88-0 (2R,3R,4R,5R)-2-benzyloxymethyl-5-[(1S)-5-{(5S,7S)-1,6-dioxa-spiro[4.5]dec-7-yl}-1-hydroxy-pentyl]-3,4-dihydroxy-pyrrolidine-1-carboxylic acid benzyl ester 
• 914649-76-6 (2R,3R,4R,5R)-2-benzyloxymethyl-5-[(1R)-5-{(5S,7S)-1,6-dioxa-spiro[4.5]dec-7-yl}-1-hydroxy-pentyl]-3,4-dihydroxy-pyrrolidine-1-carboxylic acid benzyl ester 
• 914649-82-4 (2S,5S)-2-benzyloxymethyl-5-[(1S)-5-{(5S,7S)-1,6-dioxa-spiro[4.5]dec-7-yl}-1-hydroxypentyl]-2,5-dihydro-pyrrole-1-carboxylic acid benzyl ester 
• 914649-72-2 (2S,5S)-2-benzyloxymethyl-5-[(1R)-5-{(5S,7S)-1,6-dioxa-spiro[4.5]dec-7-yl}-1-hydroxypentyl]-2,5-dihydro-pyrrole-1-carboxylic acid benzyl ester 

Relevant articles and documents

Palladium-catalyzed DYKAT of butadiene monoepoxide: Enantioselective total synthesis of (+)-DMDP, (-)-bulgecinine, and (+)-broussonetine G

Palladium catalyzed asymmetric allylic alkylation reaction of an amine with two equivalents of butadiene monoxide allows for the expedient synthesis of trans- and cis-2,5-dihydropyrroles. The versatility of these chiral synthons towards the synthesis of a wide variety of iminosugar natural products was demonstrated with the short and high yielding asymmetric syntheses of (+)-DMDP, and (-)-bulgecinine. In addition, the first total synthesis of (+)-broussonetine G, a potent glycosidase inhibitor, is described along with the assignment of its relative and absolute stereochemical configuration.

Palladium-Catalyzed DYKAT of Vinyl Epoxides: Enantioselective Total Synthesis and Assignment of the Configuration of (+)-Broussonetine G

A potential general approach to potent N-heterocyclic glycosidase inhibitors is illustrated by the first total synthesis of (+)-broussonetine G (1). The key transformation of the synthesis relies on two successive palladium-catalyzed asymmetric allylic al