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Synthesis of 4,5-disubstituted-3-deoxy-d-manno-octulosonic acid (Kdo) derivatives

✍ Scribed by Yi, Ruiqin; Ogaki, Atsushi; Fukunaga, Mayumi; Nakajima, Hiromitsu; Ichiyanagi, Tsuyoshi

Book ID: 125438473
Publisher: Elsevier Science
Year: 2014
Tongue: French
Weight: 645 KB
Volume: 70
Category: Article
ISSN: 0040-4020
DOI: 10.1016/j.tet.2014.04.024

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The 8-C-lithiated acrylamide 3A has been proven to be an ideal pyruvate 8-carbanion equivalent useful in a highly diastereoselective KDO synthesis. The starting material 3 was prepared from pyruvate diethyl acetal in four convenient steps. Direct lithiation with 2 equiv. of LDA generated the dilithi