Formation of orthoesters of oleanolic acid during Konigs-Knorr glycosidations

Authors
Seebacher, W Haslinger, E Weis, R
Citation
W. Seebacher et al., Formation of orthoesters of oleanolic acid during Konigs-Knorr glycosidations, MONATS CHEM, 132(7), 2001, pp. 839-847
Citations number
18
Categorie Soggetti
Chemistry
Journal title
MONATSHEFTE FUR CHEMIE
ISSN journal
00269247 → ACNP
Volume
132
Issue
7
Year of publication
2001
Pages
839 - 847
Database
ISI
SICI code
0026-9247(200107)132:7<839:FOOOOA>2.0.ZU;2-F
Abstract
The formation of orthoesters during Konigs-Knorr reactions is described. Di phenylmethyl oleanolate reacts with 1 --> 4 linked disaccharide donors to o rthoesters instead of the expected glycosides. The reaction with acetobromo glucose gave a mixture of orthoester and glycoside. The influence of the st ructure of the glycosyl donors and of the reaction conditions on the format ion of orthoesters is discussed.