1379002-85-3

Basic information

• Product Name: (5R,6S,8S,9S)-6-tert-butyldiphenylsilyloxymethyl-8,9-(dimethylmethylenedioxy)-3-α-naphthyl-2-selenoxo-7-oxa-1,3-diazaspiro[4.4]nonan-4-one
• Synonyms: (5R,6S,8S,9S)-6-tert-butyldiphenylsilyloxymethyl-8,9-(dimethylmethylenedioxy)-3-α-naphthyl-2-selenoxo-7-oxa-1,3-diazaspiro[4.4]nonan-4-one
• CAS NO: 1379002-85-3
• Molecular Weight: 685.754
• Mol File: 1379002-85-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (5R,6S,8S,9S)-6-tert-butyldiphenylsilyloxymethyl-8,9-(dimethylmethylenedioxy)-3-α-naphthyl-2-selenoxo-7-oxa-1,3-diazaspiro[4.4]nonan-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: (5R,6S,8S,9S)-6-tert-butyldiphenylsilyloxymethyl-8,9-(dimethylmethylenedioxy)-3-α-naphthyl-2-selenoxo-7-oxa-1,3-diazaspiro[4.4]nonan-4-one(1379002-85-3)
• EPA Substance Registry System: (5R,6S,8S,9S)-6-tert-butyldiphenylsilyloxymethyl-8,9-(dimethylmethylenedioxy)-3-α-naphthyl-2-selenoxo-7-oxa-1,3-diazaspiro[4.4]nonan-4-one(1379002-85-3)

Safety Data

• Hazardous Substances Data: 1379002-85-3(Hazardous Substances Data)

Upstream product

• 352541-83-4 5-O-tert-butyldiphenylsilyl-3-C-trichloromethyl-1,2-O-isopropylidene-β-D-lyxofuranose 
• 172751-32-5 5-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-β-D-threo-pentofuranose-3-ulose 
• 912676-30-3 α-naphthyl isoselenocyanate 
• 1379002-57-9 3-amino-3-deoxy-5-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-3-C-methoxycarbonyl-β-D-arabinofuranose 

Relevant articles and documents

Synthesis of conformationally-constrained thio(seleno)hydantoins and α-triazolyl lactones from d-arabinose as potential glycosidase inhibitors

We have explored the rich structural diversity provided by an α-azido ester derived from d-arabinose as the source of sugar templates with reduced conformational flexibility. Using transient α-thioureido(selenoureido) esters we have prepared spiranic thio(seleno)hydantoins at the C-3 position of the sugar moiety. In this context, the first example of a stable spiranic α-lactam (or aziridinone) was isolated as a by-product in the hydrogenolysis of the starting α-azido ester. Furthermore, using copper(I)-catalyzed azido-alkyne cycloaddition (click chemistry), we have accessed bicyclic cis-fused α-triazolyl lactones fixed in the furanose form. Spiranic thiohydantoins turned out to be moderate, though selective, inhibitors of glycosidases, whereas their selenium isosters behaved as good free radical scavengers.