Stereoselective synthesis of L-oliose trisaccharide via iterative alkynol cycloisomerization and acid-catalyzed glycosylation

Frank E McDonald; Minglang Wu

doi:10.1021/ol026886o

Stereoselective synthesis of L-oliose trisaccharide via iterative alkynol cycloisomerization and acid-catalyzed glycosylation

Org Lett. 2002 Oct 31;4(22):3979-81. doi: 10.1021/ol026886o.

Authors

Frank E McDonald¹, Minglang Wu

Affiliation

¹ Department of Chemistry, Emory University, 1515 Pierce Drive, Atlanta, Georgia 30322, USA. [email protected]

PMID: 12599507
DOI: 10.1021/ol026886o

Abstract

[formula: see text] The synthesis of an all-alpha L-oliose diastereomer of digitoxin provides valuable insights into the generality and protective-group dependence of acid-catalyzed glycosylations of glycals to 2-deoxycarbohydrates.

Publication types

Research Support, U.S. Gov't, Non-P.H.S.
Research Support, U.S. Gov't, P.H.S.

MeSH terms

Acids
Cyclization
Digitoxin / chemistry
Fucose / chemistry
Glycosylation
Stereoisomerism
Trisaccharides / chemical synthesis*

Substances

Acids
Trisaccharides
galactopyranosyl-1-3-glucopyranosyl-1-2-fructofuranose
Fucose
Digitoxin

Grants and funding

CA 59703/CA/NCI NIH HHS/United States