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Three-step synthesis of protected L-altrose from D-galactose derived Perlin aldehyde

Authors : Suvendu Halder, Rupa Bai Addanki and Pavan K. Kancharla*


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Abstract

A new short three-step strategy has been designed for the synthesis of L-hexoses that are rare antipodes of the common hexoses from the commercially available glycals. SN2 inversion of the triflate derived from the easily accessible Perlin aldehydes, followed by the dihydroxylation, leads to L-hexoses in good yields. The strategy has been successfully demonstrated by synthesizing one of the most expensive L-sugars i.e. L-altrose from D-galactose derived Perlin aldehyde. Also, interesting reactivity of the 2,4-dintrosulfonate group and the reactivity of protected Perlin aldehydes under the oxidative conditions have been discussed.

Keyword

Glycals, Perlin aldehyde, SN2 inversion, L-sugars