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Org Lett. 2014 May 16;16(10):2776-9. doi: 10.1021/ol501101f. Epub 2014 May 1.

Scope and limitations of 2-deoxy- and 2,6-dideoxyglycosyl bromides as donors for the synthesis of β-2-deoxy- and β-2,6-dideoxyglycosides.

Author information

1
Department of Chemistry, Yale University , New Haven, Connecticut 06520, United States.

Abstract

It is shown that 2-deoxy- and 2,6-dideoxyglycosyl bromides can be prepared in high yield (72-94%) and engaged in glycosylation reactions with β:α selectivities ≥6:1. Yields of product are 44-90%. Fully armed 2-deoxyglycoside donors are viable, while 2,6-dideoxyglycosides require one electron-withdrawing substituent for high efficiency and β-selectivity. Equatorial C-3 ester protecting groups decrease β-selectivity, and donors bearing an axial C-3 substituent are not suitable. The method is compatible with azide-containing donors and acid-sensitive functional groups.

PMID:
24786757
PMCID:
PMC4033630
DOI:
10.1021/ol501101f
[Indexed for MEDLINE]
Free PMC Article

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