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2,5-Dioxabicyclo[2.2.2]octan-Derivate: Konformation von Methyl-2,6-anhydro-α-D-hexopyranosiden (1980)

Köll, Peter ; Komander, Herbert ; Kopf, Jürgen

Weinheim : Wiley-Blackwell

Berichte der deutschen chemischen Gesellschaft 113 (1980), S. 3919-3926

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ISSN: 0009-2940

Keywords: Chemistry ; Inorganic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: 2,5-Dioxabicyclo[2.2.2]octane Derivatives: Conformation of Methyl 2,6-Anhydro-α-D-hexopyranosidesRing opening of methyl 2,6:3,4-dianhydro-α-D-altropyranoside (5) with KOH in water at 150°C yields almost exclusively the hitherto unknown methyl 2,6-anhydro-α-D-mannopyranoside (6). 1H NMR spectra of this compound and of all other α-anomers of this series suggest a conformation of the pyranose ring intermediate between the boat 2,5B(D) and the twist boat 5S1(D). This was verified by X-ray analysis of methyl 3,4-di-O-acetyl-2,6-anhydro-α-D-altropyranoside (2).

Additional Material: 2 Ill.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/cber.19801131225

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