It is well known that naturally occurring sialo compounds such as glycoproteins and glycolipids in cell membranes, which play important roles in biological systems'-', contain sialic acids in a-glycosidic linkage. Therefore, a facile, a-selective synthesis of sialic-acid glycosides is very important
Stereoselective synthesis of 2-thioglycosides of N-acetylneuraminic acid
✍ Scribed by Alberto Marra; Pierre Sinaÿ
- Publisher
- Elsevier Science
- Year
- 1989
- Tongue
- English
- Weight
- 628 KB
- Volume
- 187
- Category
- Article
- ISSN
- 0008-6215
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We have continued our work to develop novel analogues of sialic acid [1-4] that may specifically modulate the interaction between endogenous sialic acid and influenza virus haemagglutinin [3,5,6]. Functional groups of sialic acid that have been implicated for this virus-host recongnition are the gly
A new synthesis of N-acetylneuraminic acid (NeuSAc; 28) via the aldehyde 10 is described. The aldehyde 10 was obtained from N-acetyl-o-glucosamine (11; 5 steps, overall yield ca. 6 %) or from o-glucono-1,s-lactone (17; 6 steps, overall yield ra. 57%). Thus, on the one hand, N-acetyl-D-mannosamine (1