Efficient Synthesis of 2α-Glycoside ofN-Acetylneuraminic Acid via Phenylsulfenyl Chloride Adduct of 2-Deoxy-2,3-dehydro-N-acetylneuraminic Acid Methyl Ester Tetra-O-acetate

1988 ◽  
Vol 17 (10) ◽  
pp. 1657-1660 ◽  
Author(s):  
Tadao Kondo ◽  
Hiroyuki Abe ◽  
Toshio Goto
Keyword(s):  
Methyl Ester ◽  
Acid Methyl Ester ◽  
Efficient Synthesis ◽  
Acetylneuraminic Acid ◽  
Acid Methyl ◽  
Chloride Adduct

scholarly journals Functionalization of 2-Deoxy-2,3-dehydro-N-acetylneuraminic Acid Methyl Ester

1987 ◽  
Vol 60 (2) ◽  
pp. 631-636 ◽  
Author(s):  
Kaoru Okamoto ◽  
Tadao Kondo ◽  
Toshio Goto
Keyword(s):  
Methyl Ester ◽  
Acid Methyl Ester ◽  
Acetylneuraminic Acid ◽  
Acid Methyl

Rapid and clean microwave-assisted synthesis of N-acetylneuraminic acid methyl ester and its β-methyl glycoside

2012 ◽  
Vol 53 (46) ◽  
pp. 6254-6256 ◽  
Author(s):  
Pradeep Chopra ◽  
Robin J. Thomson ◽  
I. Darren Grice ◽  
Mark von Itzstein
Keyword(s):  
Methyl Ester ◽  
Acid Methyl Ester ◽  
Microwave Assisted Synthesis ◽  
Methyl Glycoside ◽  
Acetylneuraminic Acid ◽  
Microwave Assisted ◽  
Acid Methyl

scholarly journals Koenigs-Knorr Glycosylation with Neuraminic Acid Derivatives

2010 ◽  
Vol 2010 ◽  
pp. 1-8 ◽  
Author(s):  
Galina Pazynina ◽  
Vitaly Nasonov ◽  
Ivan Belyanchikov ◽  
Reinchard Brossmer ◽  
Maxim Maisel ◽  
...  
Keyword(s):  
Methyl Ester ◽  
Acid Methyl Ester ◽  
Neuraminic Acid ◽  
Carbohydrate Binding ◽  
Acetylneuraminic Acid ◽  
Acid Methyl ◽  
Glycosyl Donor ◽  
Carbohydrate Binding Proteins ◽  
Derivatives Of

Earlier we reported a convenient and efficient method of preparing α2-6 sialooligosaccharides in conditions of Koenigs-Knorr reaction. The use of Ag2CO3 allowed carrying out α2-6 sialylation of galacto-4,6-diol of mono- and disaccharides with chloride of acetylated N-acetylneuraminic acid methyl ester as glycosyl donor. In this study we applied this approach to other derivatives of neuraminic acid, namely, Neu5Gc, 9-deoxy-9-NAc-Neu5Ac, Neu5Acα2-8Neu5Ac, and Neu5Acα2-8Neu5Acα2-8Neu5Ac as glycosyl donors; eight compounds were synthesized: Neu5Gcα-O(CH2)3NH2 (8), Neu5Gcα2-6Galβ1-4GlcNAcβ-O(CH2)3NH2 (10), 9-deoxy-9-NAc-Neu5Ac-O(CH2)3NH2 (15), 9-deoxy-9-NAc-Neu5Acα2-6Galβ1-4GlcNAcβ-O(CH2)3NH2 (17), Neu5Acα2-8Neu5Acα-O(CH2)3NH2(23) Neu5Acα2-8Neu5Acα-OCH3 (24), Neu5Acα2-8Neu5Acα-OCH2(p-C6H4)NHCOCH2NH2 (25), and Neu5Acα2-8Neu5Acα2-8Neu5Acα-O(CH2)3NH2 (32). These sialosides were used for characterization of siglecs and other carbohydrate-binding proteins.

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