CONVENIENT SYNTHESIS OF PYRUVATE ACETALS OF CARBOHYDRATES BY COUPLINGOF TRIALKYLSILYLATED DIOLS AND PYRUVATES

Authors
HIRUMA K TAMURA J HORITO S YOSHIMURA J HASHIMOTO H
Citation
K. Hiruma et al., CONVENIENT SYNTHESIS OF PYRUVATE ACETALS OF CARBOHYDRATES BY COUPLINGOF TRIALKYLSILYLATED DIOLS AND PYRUVATES, Tetrahedron, 50(42), 1994, pp. 12143-12158
Citations number
24
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
42
Year of publication
1994
Pages
12143 - 12158
Database
ISI
SICI code
0040-4020(1994)50:42<12143:CSOPAO>2.0.ZU;2-I
Abstract
Hexopyranoside diols, mainly 4,6-diols with alpha-gluco, beta-gluco, a lpha-galacto, beta-galacto, and alpha-manno configurations could be co nverted effectively (40 - 74% yields), to the corresponding pyruvate a cetals by the coupling of the O-trialkylsilylated, namely, O-TBDMS and /or O-TMS diols, and ethyl pyruvate in the presence of TMSOTf at tempe ratures between -30 degrees C and +3 degrees C. In the case of the bet a-manno isomer, the anomerization of the beta-glycoside to the alpha-g lycoside as well as the ring contraction of the pyranoside to the fura noside predominated.