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Synthesis of β‑C‑Glycopyranosyl Aldehydes and 2,6-Anhydro-heptitols

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journal contribution
posted on 06.11.2015, 00:00 by Vinod Khatri, Amit Kumar, Balram Singh, Shashwat Malhotra, Ashok K. Prasad
A convenient route has been developed for the diastereoselective synthesis of β-C-glycopyranosyl aldehydes from d-glucose, d-mannose, and d-galactose. The key step in the synthesis of C-glycosyl aldehydes is the aryl driven reductive dehydration on 1-phenyl-2-(2′,3′,4′,6′-tetra-O-acetyl-β-d-glycopyranosyl)­ethanone to afford alkenes, which on oxidation afford the desired compounds in good yield. β-C-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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