82159-62-4Relevant academic research and scientific papers
A General Method for the Divergent Synthesis of C-9 Functionalised Sialic Acid Derivatives
Hassan, Abdullah A.,Oscarson, Stefan
, p. 6102 - 6108 (2020/10/02)
Sialic acids, a ubiquitous family of sugars shown to be involved in numerous biologically important processes, exhibit remarkable structural diversity in nature. Access to these derivatives by chemical and enzymatic means is a major bottle neck in understanding the role played by each particular modification. As part of a program to study such roles and determine the substrate specificity of novel sialic acid aldolases, a general and robust synthetic protocol was devised to gain access to all naturally occurring C-9 functionalised N-acetylneuraminic acid derivatives including esters. These derivatives were synthesised in 11 linear steps from a common advanced intermediate, which allowed for divergent modification at the C-9 position. Four substitutions were installed in this study: O-acetyl, O-lactyl, O-SO3, O-PO3. This synthetic pathway includes both an effective way to benzylate neuraminic acid derivatives, as well as a working methodology towards unnatural β-linked neuraminic acid glycosides.
SYNTHESES OF (α2-9) AND (α2-8) LINKED NEURAMINYLNEURAMINIC ACID DERIVATIVES
Okamoto, Kaoru,Kondo, Tadao,Goto, Toshio
, p. 5229 - 5232 (2007/10/02)
A newly prepared glycosyl donor, the acetyl protected 2β-bromo-3β-hydroxy-N-acetylneuraminic ester was condensed with the protected 2-deoxy-2,3-dehydroneuraminic ester having a free hydroxy group at 9- or 8-position to form NeuAc(α2-9)NeuAc and NeuAc(α2-8)NeuAc linkage, respectively, which are involved in the group C meningococcal polysaccharides and gangliosides.The obtained 3β-hydroxy disaccharides were phenoxythiocarbonylated, reduced with tri-n-butylstannane, and deprotected to give the free glycosides in high yields.
