Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2004, Issue 16, Pages 3435-3446Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200400069
Keywords
baccatin III; glycosidation; glycoconjugates; multistep synthesis; polymer-bound reagents; protecting group
Categories
Ask authors/readers for more resources
Polymer-bound diphenylphosphane hydrobromide 2 shows excellent properties in the activation of enol ethers and glycals, the introduction and cleavage of THP ethers being promoted with excellent yields with this functionalized polymer. Glycosidations of glycals work equally well, with suppression of the formation of undesired Ferrier rearranged products. The reagent is sufficiently mild to leave labile 2-deoxy glycosidic bonds and acid-labile protecting groups intact. It can be employed to transfer disaccharide glycosyl donors onto aglycons and is also selective for the promotion of two glycosidations in one pot. Highly hindered glycosyl donor groups such as the hydroxy group at C-13 of the baccatin III framework can be glycosylated with glycals in the presence of this polymer-bound reagent. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available