ISSN:
0009-2940
Keywords:
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
Syntheses of Biologically Important Carbohydrates, 27. Total Synthesis and Determination of the Configuration of -Branched 2,3,6-Trideoxy HexosesAfter cis-hydroxylation of DL-trans-3-methyl-3-tosylamino-4-hexenal ethylene acetal (3a-4a) followed by hydrolysis, glycosidation and acetylation the anomeric forms of the methyl 4-0-acetyl-2,3,6-trideoxy-3-C-methyl-3-tosylamino-DL-hexopyranosides with lyxo- (α-14, β-15) and xylo-configuration (α-16, β-17) are obtained. Detailed spectroscopical investigations with 14-17 and with (3R)- (21) and (3s)-methyl-4-0-benzoyl-2,3,6-trideoxy-3-C-methyl-α-D-erythro-hexo-pyranoside (22) respectively, show relationships between 1H NMR parameters and the configurations at the branching point.
Notes:
Nach cis-Hydroxylierung von DL-trans-3-Methyl-3-tosylamino-4-hexenal-ethylenacetal (3a, 4a) werden nach Hydrolyse, Glycosidierung und Acetylierung die anomeren Methyl-4-O-acetyl- 2,3,6-tridesoxy-3-C-methyl-3-tosylamino-DL-hexopyranoside mit lyxo- (α-14, β-15) und xylo-Konfiguration (α-16, β-17) getrennt erhalten. Detaillierte spektroskopische Untersuchungen an 14-17 und an (3R)- (21) bzw, (3s)-Methyl-4-0-benzoyl-2,3,6-tridesoxy-3-C-methyl-α-D-erythro-hexopyranosid (22) führen zu Zusammenhängen zwischen 1H—NMR-Parametern und den Konfigurationen am Verzweigungsort.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19811140802
