ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
C-Glycosides of N-Acetylneuraminic AcidThe synthesis of the C-glycosides 8, 15, and 9 of N-acetylneuraminic acid is described. Hydroxymethylation of the Li-ester enolate, derived from 5, yielded the protected C-glycosides 7 and 10 (46%; 3:1), which were deprotected to yield 8 (54%) and 15 (51%; Scheme 2). The mesylate 16 was obtained from 7 (73%) and transformed via the azide 17 (75%) into the acid 18 (66%) and the amino acid 9 (Scheme 3). The configuration at C(2) of 17 was proved by transforming 17 into the bicyclic lactam 19. Both 8 and 15 are very weak inhibitors of Vibrio cholerae sialidase; 9 appears to stimulate this enzyme.
Additional Material:
7 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19910740716
