Structural variations of N??acetylneuraminic acid, 15. Synthesis of 9??deoxy??, 7, 9??dideoxy??, and 4, 7, 9??trideoxy??N??acetylneuraminic acid and their behaviour towards …

E Schreiner, R Christian, E Zbiral

Index: Schreiner, Erwin; Christian, Rudolf; Zbiral, Erich Liebigs Annalen der Chemie, 1990 , # 1 p. 93 - 97

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Citation Number: 16

Abstract

Abstract The methyl ester of N-acetylneuraminic acid β-methyl ketoside (Neu5Ac1Me-2β- Me)(1) is used as common starting material for the synthesis of the title compounds. Combined derivatization reactions with reagents thiophosgene, p-cresol, benzoyl chloride, and acetic anhydride/pyridine lead to the thiocarbonate derivatives 2, 6–8, and 12. Further transformation with iodomethane yields the 9-iodo compounds 3, 9, and 13, which are ...