jo5b01933_si_001.pdf (1.5 MB)
Synthesis of β‑C‑Glycopyranosyl Aldehydes and 2,6-Anhydro-heptitols
journal contribution
posted on 2015-11-06, 00:00 authored by Vinod Khatri, Amit Kumar, Balram Singh, Shashwat Malhotra, Ashok K. PrasadA 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.