ISSN:
0009-2940
Keywords:
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
Carboxonium Compounds in Carbohydrate Chemistry, XX. Neighbouring-group Reaction of 1,6-Anhydro-α-D-galactofuranose to 1,6-Anhydro-α-D-talofuranose and Ring Contraction to 1,5-Anhydro-α-D-talofuranose by the Action of Trifluormethanesulfonic AcidTreatment of tri-O-acetyl-l,6-anhydro-α-D-galactofuranose with trifluoromethanesulfonic acid produces the acetoxonium compounds 1 and 6 and leads to the formation of 1,6-anhydro-α-D-talofuranose (10) and 1,5-anhydro-α-D-talofuranose (1,4-anhydro-β-D-talopyranose) (12), respectively, after hydrolysis, acetylation, and deesterification. The structure of 12 was confirmed by its conversion to the known 6-deoxy derivative 15.
Notes:
Einwirkung von Trifluormethansulfonsäure auf Tri-O-acetyl-1,6-anhydro-α-D-galactofuranose (2) führt über die Acetoxoniumverbindungen 1 und 6 nach Hydrolyse, Acetylierung und Entblockierung zur 1,6-Anhydro-α-D-talofuranose (10) und 1,5-Anhydro-α-D-talofuranose (1,4-Anhydro-β-D-talopyranose) (12) Die Struktur von 12 wurde durch Überführung in das bekannte 6-Desoxyderivat 15 bewiesen.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19731060730
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