360562-51-2

Upstream product

• 53215-95-5 N-(trimethylsilylmethyl)benzylamine 
• 100-46-9 benzylamine 
• 360562-48-7 1,1-Dibromo-5-[(tert-butyldimethylsilyl)oxy]-1,2-dideoxy-3,4-O-(1-methylethylidene)-L-threo-pent-1-ene 
• 108817-97-6 (4R,5S)-5-tert-butyldimethylsilyloxymethyl-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde 
• 360562-49-8 5-[(tert-Butyldimethylsilyl)oxy]-1,2-dideoxy-3,4-O-(1-methylethylidene)-L-threo-pent-1-yne 
• 360562-50-1 1,2-Dideoxy-3,4-O-(1-methylethylidene)-L-threo-pent-1-ynitol 

Downstream Products

• 360562-53-4 [(3aS,7S,7aS)-5-Benzyl-2,2-dimethylhexahydro[1,3]dioxolo[4,5-c]pyridin-7-yl]methanol 
• 215725-14-7 N-benzyl (-)-isofagomine 
• 275363-98-9 (3S,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)piperidine 
• 360562-52-3 (3aS,7aS)-5-benzyl-2,2-dimethyl-7-methylenehexahydro-[1,3]dioxolo[4,5-c]pyridine 

Relevant academic research and scientific papers

A novel approach to both the enantiomers of potent glycosidase inhibitor isofagomine via PET-promoted cyclization of 1-[benzyl(trimethylsilylmethyl)amino]-1,4,5-trideoxy-2,3-O-(1- methylethylidene)-threo-pent-4-ynitol

The cyclization of PET-generated α-trimethylsilylmethylamine radical cation to a tethered acetylene moiety has been exploited to solve the problem of the generation of an aminomethyl group next to a stereocenter in the synthesis of 1-N-iminosugar type glycosidase inhibitors. Its success is demonstrated by the synthesis of (+)- as well as (-)-isofagomine, an extremely potent β-glucosidase inhibitor of the 1-N-iminosugar class.

A general strategy towards the synthesis of 1-N-iminosugar type glycosidase inhibitors: Demonstration by the synthesis of D- as well as L-glucose type iminosugars (isofagomines)

Both enantiomers of isofagomine, the potent glycosidase inhibitor of a type 1-N-iminosugar have been synthesized by the intramolecular cyclization of the PET generated α-trimethylsilylmethylamine radical cation with the appropriate tethered acetylene moiety. (C) 2000 Published by Elsevier Science Ltd.