Synthesis of enantiopure C-glycosides and pseudo C-glycosides: Lewis-acid mediated heterolysis of methyl acetals

Authors
Gaertzen, O Misske, AM Wolbers, P Hoffmann, HMR
Citation
O. Gaertzen et al., Synthesis of enantiopure C-glycosides and pseudo C-glycosides: Lewis-acid mediated heterolysis of methyl acetals, TETRAHEDR L, 40(35), 1999, pp. 6359-6363
Citations number
22
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
35
Year of publication
1999
Pages
6359 - 6363
Database
ISI
SICI code
0040-4039(19990827)40:35<6359:SOECAP>2.0.ZU;2-F
Abstract
Lewis-acid mediated heterolysis of substituted methoxy acetals derived from anomeric [3.3.1] oxabicyclic lactones leads to enantiopure deoxy C-glycosi des in excellent chemical yield. An alternative route to C-glycosidic ester s involves simple one-step opening of [3.3.1] oxabicyclic lactones with in situ esterification. (C) 1999 Elsevier Science Ltd. All rights reserved.