ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
N-Acetylneuraminic acid (1) can be transformed into the methyl α-D-ketoside 2 which, by reaction with methanesulfonyl chloride, yields the corresponding 4-O-mesylate 3 and the 4,7-di-O-mesylate 4 as a by-product. Compound 3 reacts with Nal giving the 4-deoxy-4-iodo compound 5 with equatorial orientation of the I-atom. As second product, the dihydrooxazole 6 is produced. Catalytic hydrogenation of 5 is followed by ester cleavage and removal of the isopropylidene group yielding the methyl α-D-ketoside 8 which affords the title compound, N-acetyl-4-deoxyneuraminic acid (9), by reaction with fowl plague virus sialidase. Further biochemical activities of 8 and 9 are reported.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19860690837
