ISSN:
0170-2041
Keywords:
2-Deoxyglycosides
;
Glycosylation, stereoselective
;
Glycosyl fluorides, 2-deoxy-
;
Lewis acid catalysis
;
Carbohydrates
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
3,4-Di-O-acetyl-2,6-dibromo-2,6-dideoxy-α-D-mannopyranosyl fluoride (1) was treated with Lewis acid catalysts to give α-glycosides exclusively. Reactions with α- and β-glucosyl analogs yield α/β mixtures under the same conditions. With no assistance of anchimeric substituents at C-2 the stereoselectivity is directed by a glycosyl fluoride/catalyst/solvent complex. As shown in the 2-deoxy-arabino-hexopyranosyl series this leads to improved α/β ratios and yields.
Additional Material:
2 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.1991199101130
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