247044-34-4Relevant academic research and scientific papers
Synthesis of C11 chain-extended analogues of N-acetylneuraminic acid
Kiefel, Milton J.,Bennett, Simon,Von Itzstein, Mark
, p. 439 - 442 (1996)
The synthesis of novel C11 chain-extended analogues of N-acetylneuraminic acid has been achieved from the N-acetyl-9-hydroxyneuraminic acid derivative 7 via a Swern oxidation/Wittig olefination sequence. In this way the novel α,β-unsaturated es
A facile synthesis of Neu5Ac2en derivatives from the glycosides of TV-acetylneuraminic acid
Kok, Gaik B.,Groves, Darrin,Von Itzstein, Mark
, p. 2109 - 2115 (2007/10/03)
In a onerpot reaction, acetolysis of some functionalised methyl glycosides of W-acetylneuraminic acid (NeuSAc) methyl ester provides a direct and efficient entry into the corresponding 2,3-imsaturated (Neu5Ac2en) derivatives. Other glycosides of NeuSAc, such as benzyl and 2-(trimethylsilyl)ethyl glycosides, like their methyl counterpart, are also transformed into the 2,3-unsaturated analogues. This reaction has also been applied to the synthesis of some novel 4-bis-substituted-Neu5Ac2en derivatives, which in turn has led to the synthesis of the C-4 homologue of the per-acetylated methyl ester of Neu5Ac2en, compound 10.
