DIRECT SYNTHESIS OF MONO-GLYCOSYLATED CATECHOLS FROM GLYCOSYLACETATESOR IMIDATES USING BF3. OET(2) AS CATALYST1

Authors
MABIC S BENEZRA C LEPOITTEVIN JP
Citation
S. Mabic et al., DIRECT SYNTHESIS OF MONO-GLYCOSYLATED CATECHOLS FROM GLYCOSYLACETATESOR IMIDATES USING BF3. OET(2) AS CATALYST1, Tetrahedron letters, 34(28), 1993, pp. 4531-4534
Citations number
15
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
34
Issue
28
Year of publication
1993
Pages
4531 - 4534
Database
ISI
SICI code
0040-4039(1993)34:28<4531:DSOMCF>2.0.ZU;2-6
Abstract
The coupling of 3-n-alkylcatechols to the acetate or trichloroimidate derivatives of beta-D- or alpha-D- sugars (glucose, galactose. xylose, mannose and maltose) catalysed by BF3.OEt2 has been studied. Beta sug ars with an equatorial acetate group at position 2 formed exclusively beta adducts with yields of 60-80%. Alpha sugars with an equatorial ac etate group at position 2 formed beta adducts, while beta sugars with an axial acetate group formed alpha adducts when activated as trichlor oimidates, with yields of 70-85%. Two mechanisms to explain these resu lts are proposed.