Synthetic Studies on Sialoglycoconjugates 17: Synthesis of 4-O-, 9-O-, and 4,9-Di-O-Acetyl-N-Acetylneuraminic Acids and their Derivatives
- 1 January 1990
- journal article
- research article
- Published by Taylor & Francis in Journal of Carbohydrate Chemistry
- Vol. 9 (4) , 415-428
- https://doi.org/10.1080/07328309008543842
Abstract
4-O-, 9-O-, and 4,9-Di-O-acetyl derivatives 9, 13, and 23 of N-acetylneuraminic acid were synthesized from methyl (methyl 5-acetamido-3,5-di-deoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)onate (1) or methyl [2-(trimethylsilyl)ethyl 5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosid)onate (14). In addition, the suitably protected derivatives 7 and 11 of the 4-O- and 9-O-acetyl derivatives, which could be used as the glycosyl donors for the synthesis of gangliosides containing the O-acetyl group at C-4 or C-9 in N-acetylneuraminic acid moiety, were synthesized.This publication has 18 references indexed in Scilit:
- A facile, regio- and stereo-selective synthesis of ganglioside GM3Carbohydrate Research, 1989
- Synthetic Studies on Sialoglycoconjugates. 5: A Facile, Regio and Stereoselective Synthesis of Ganglioside GM4and Its Position Isomer1Journal of Carbohydrate Chemistry, 1989
- Synthetic Studies on Sialoglycoconjugates. 3: Synthesis of 5-Acetamido-3,5-Dideoxy-l-Arabino-2-Heptulosonic Acid Derivatives and AnalogsJournal of Carbohydrate Chemistry, 1989
- A facile regio- and stereo-selective synthesis of α-glycosides of N-acetylneuraminic acidCarbohydrate Research, 1988
- 2-(Trimethylsilyl)ethyl glycosides. 3. Synthesis, anomeric deblocking, and transformation into 1,2-trans 1-O-acyl sugarsThe Journal of Organic Chemistry, 1988
- Glycosylation Using Methylthioglycosides ofN-Acetylneuraminic Acid and Dimethyl(Methylthio)Sulfonium TriflateJournal of Carbohydrate Chemistry, 1988
- An efficient approach to streoselective glycosylation of N-acetylneuraminic acid: Used of phenylselenyl group as a stereocontrolling auxillaryTetrahedron Letters, 1987
- Boron trifluoride etherate as an effective reagent for the stereoselective one-pot conversion of acetylated 2-trimethylsilylethyl glycosides into sugar 1,2-trans-acetatesTetrahedron Letters, 1986
- An effective synthesis of α-glycosides of
- A novel promoter for the efficient construction of 1,2-trans linkages in glycoside synthesis, using thioglycosides as glycosyl donorsCarbohydrate Research, 1986