NOUVELLE SYNTHESE DE SPIRO-ORTHOESTERS D-GLUCOSIDIQUES PAR PHOTOCYCLISATION STEREOSELECTIVE D'HYDROXYALKYL-D-GLUCOSIDES

Article abstract of DOI:10.1016/0008-6215(84)85081-8

Irradiation of hydroxyalkyl glucosides in the presence of mercury(II) oxide and iodine gave glucosidic C-1-spiroorthoesters.Where the starting glycoside had CH2OH, the cyclization was regio- and stereo-specific by α-attack.The C-1-spiroorthoesters were readily available in a "one-pot synthesis" starting from glucosyl halides.