Synthesis of β‑<i>C</i>‑Glycopyranosyl Aldehydes and 2,6-Anhydro-heptitols


A convenient route has been developed for the diastereoselective synthesis of β-<i>C</i>-glycopyranosyl aldehydes from d-glucose, d-mannose, and d-galactose. The key step in the synthesis of <i>C</i>-glycosyl aldehydes is the aryl driven reductive dehydration on 1-phenyl-2-(2′,3′,4′,6′-tetra-<i>O</i>-acetyl-β-d-glycopyranosyl)­ethanone to afford alkenes, which on oxidation afford the desired compounds in good yield. β-<i>C</i>-Glycopyranosyl aldehydes have been converted to 2,6-anhydro-heptitols in quantitative yields. The 2,6-anhydro-heptitols derived from d-mannose and d-galactose are enantiomeric and are useful linkers for the synthesis of macrocycles/amphiphiles of complementary chirality

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oai:figshare.com:article/2111932Last time updated on 2/12/2018

This paper was published in FigShare.

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