ISSN:
1434-4475
Keywords:
9,8,7,6-Tetra-O-acetyl-N-acetylneuraminic acid-γ-lactone, synthesis of
;
N-Acetylneuraminic acid-γ-lactone diethyldithioketale
;
Sylilation with t-butyldimethylchlorosilane and TIPSiCl2
;
6,7-Carbonate ofN-Acylneuraminic acid-γ-lactone diethyldithioketal
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Abstract Partial protection of diethyldithioketal ofN-acetylneuraminic acid-γ-lactone using one or two equivalents oft-butyldimethylchlorosilane leads to the 9-O-silyletherderivative7 and the 8,9-bis-O-silylderivative5, resp. The reaction of1 as well as7 with 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane (TIPSiCl2) yields selectively the protected products4 and9. The 9,8,7,6-tetra-O-acetyl-N-acetylneuraminic acid-γ-lactone derivative3 is formed by the oxidative desulfurazation of the peracteylated form of1 (i. e.2) by means ofNBS. By reaction of5 withTPPDEAD the 6,7-carbonato compound6 arises instead of the expected 6,7-epoxyderivative. The analogous carbonate8 is formed by treating7 with bisimidazolylcarbonate.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF00798461
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