STEREOSELECTIVE PHASE-TRANSFER-CATALYZED SYNTHESES OF GLYCOSYLOXYSUCCINIMIDES AND THEIR TRANSFORMATIONS INTO GLYCOPROBES

Authors
CAO SD TROPPER FD ROY R
Citation
Sd. Cao et al., STEREOSELECTIVE PHASE-TRANSFER-CATALYZED SYNTHESES OF GLYCOSYLOXYSUCCINIMIDES AND THEIR TRANSFORMATIONS INTO GLYCOPROBES, Tetrahedron, 51(24), 1995, pp. 6679-6686
Citations number
22
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
51
Issue
24
Year of publication
1995
Pages
6679 - 6686
Database
ISI
SICI code
0040-4020(1995)51:24<6679:SPSOG>2.0.ZU;2-U
Abstract
Glycosyloxysuccinimides of D-galactose, D-glucose, N-acetyl-D-glucosam ine, Lactose, maltose (7-11) and sialic acid (13) were prepared from t heir glycosyl halides under PTC conditions. Ring opening of the succin imide moieties occurred with sodium hydroxide or methoxide to provide extended aglycons, while treatment of 8 with hydrazine afforded O-gala ctopyranosylhydroxylamine 17. Treatment of 9 with tris(2-aminoethyl)am ine gave divalent cluster 20 which upon further treatment with fluores cein isothiocyanate provided divalent glycoprobe 21.