SYNTHESIS OF DIULOSES BY CHAIN ELONGATION OF ALDONOYL CHLORIDES

Authors
MEISEL R PESEKE K REINKE H
Citation
R. Meisel et al., SYNTHESIS OF DIULOSES BY CHAIN ELONGATION OF ALDONOYL CHLORIDES, Journal fur praktische Chemie, Chemiker-Zeitung, 340(3), 1998, pp. 264-268
Citations number
13
Categorie Soggetti
Chemistry,"Chemistry Applied
Journal title
Journal fur praktische Chemie, Chemiker-Zeitung → ACNP
ISSN journal
09411216
Volume
340
Issue
3
Year of publication
1998
Pages
264 - 268
Database
ISI
SICI code
0941-1216(1998)340:3<264:SODBCE>2.0.ZU;2-Q
Abstract
2,3,4,5,6-Penta-O-acetyl-D-galactonic acid chloride (la) and D-gluconi c acid chloride (Ib), respectively, react with alkyl acetoacetates and benzoylacetates 2, respectively, to yield derivatives 3 of diuloses w ith an alkoxycarbonyl group in the branch. Decarboalkoxylation of thes e compounds gives 1,3-didesoxy-nono-2,4-diuloses 4a,b and 2-deoxy-octo -1,3-diuloses 4c, respectively. Compound 4a and diazomethane react to furnish the corresponding methyl enol ether 5a and 5b.