ISSN:
0170-2041
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
Facile Syntheses of Galacto- and Glucopyranosyl Azides Substituted at C-6Acetylated 6-chloro-, 6-bromo-, 6-iodo-, and 6-azido-6-deoxy-α-D-glucopyranosyl azides (26, 22, 17, 30), -β-D-glucopyranosyl azides (27, 23, 18, 31), -α-D-galactopyranosyl azides (29, 25, 20, 32), and -β-D-galactopyranosyl azides (29, 25, 20, 33) have been obtained by nucleophilic displacement reactions of the appropriate 6-O-(p-toluenesulfonates) 9-12. Hydrogen iodide elimimation from the 6-iodo-6-deoxyglycosyl azides 17-20 by DBU or DBN leads to the hex-5-enopyranosyl azides with α-D-xylo (43), β-D-xylo (44), α-L-arabino (46), and β-L-arabino configuration. The structures, anomeric configurations, and conformations of the products were determined by 1H-NMR spectroscopy.
Notes:
Acetylierte 6-Chlor-, 6-Brom-, 6-Iod- und 6-Azido-6-desoxy-Derivate des α-D-Glucopyranosylazids (26, 22, 17, 30) und β-D-Glucopyranosylazids (27, 23, 18, 31) sowie des α-D-Galactopyranosylazids (28, 24, 19, 32) und β-D-Galactopyranosylazids (29, 25, 20, 33) wurden durch nucleophile Substitutionsreaktionen der entsprechenden 6-O-(p-Toluolsulfonate) 9-12 gewonnen. Die Dehdroiodierung der 6-Iod-6-desoxyazide 17-20 mit DBU oder DBN führte zu den Hex-5-enopyranosylaziden mit α-D-xylo- (43) und β-D-xylo- (44), sowie α-L-arabino- (46) und β-L-arabino-Konfiguration (45). Die Strukturen, die anomeren Konfigurationen und die Konformationen der Produkte werden durch 1H-NMR-Spektroskopie bestimmt.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.198719870314
