Intramolecular Michael addition of benzylamine to sugar derived α, β - unsaturated ester: a new diastereoselective synthesis of higher homologue of 1-deoxy- L-ido-nojirimycin

Desai, Vijaya N. ; Saha, Nabendu N. ; Dhavale, Dilip D. (1999) Intramolecular Michael addition of benzylamine to sugar derived α, β - unsaturated ester: a new diastereoselective synthesis of higher homologue of 1-deoxy- L-ido-nojirimycin Chemical Communications (17). pp. 1719-1720. ISSN 1359-7345

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Official URL: http://pubs.rsc.org/en/content/articlelanding/1999...

Related URL: http://dx.doi.org/10.1039/A905440E

Abstract

The diastereoselective intramolecular Michael addition of the benzylamine generated in situ from hemiacetal 3 leads to the lactone 4a with the required homoazasugar ring skeleton; reduction of the lactone functionality and removal of the protecting groups afford 1-deoxy-L-ido-homonojirimycin.

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