ISSN:
0170-2041
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
Cycloaddition with Unsaturated Carbohydrates, IV. - The Diels-Alder Reaction of 1,2,4,5-Tetrazine with 1,5-Anhydrohex-1-enitolsBy Diels-Alder reaction with inverse electron demand of dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate (2) and 3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-D-arabino- (1a) and -lyxo-hex-1-enitol (1b), dimethyl 4-[(1S,2R,3R)-1,2,4-triacetoxy-3-hydroxybutyl]-3,6-pyridzinedicarboxylate (5a) and the (1R,2R,3R) epimer 5b are formed by opening the sugar cyclus. Compounds 5a and b were converted into the oxo derivatives 6a and 6b. Dimethyl 3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-D-arabino-(4b) and -D-lyxo-hex-1-enitolo[1,2-d]pyridazine-3,6-dicarboxylate (4b) are by-products of the addition reaction.
Notes:
Die Diels-Alder-Reaktion mit inversem Elektronenbedarf von 1,2,4,5-Tetrazin-3,6-dicarbonsäure-dimethylester (2) mit 3,4,6-Tri-O-acetyl-1,5-anhydro-2-desoxy-D-arabino-(1a) und-lyxo-hex-1-enitol (1b) führt unter Öffnung des Zuckerringes zu 4-[(1S,2R,3R)-1,2,4-Triacetoxy-3-hydroxy-butyl]-3,6-pyridazindicarbonsäure-dimethylester (5a) und dem (1R,2R,3R)-Epimeren 5b. Diese Verbindungen wurden in die Oxo-Verbindungen 6a und 6b umgewandelt. Als Nebenprodukte der Addition entstehen 3,4,6-Tri-O-acetyl-1,5-anhydro-2-desoxy-D-arabino-(4a) und -D-lyxo-hex-1-enitolo[1,2-d]pyridazin-3′,6′-dicarbonsäure-dimethylester.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.198519850324
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