3-Azido-3-deoxy-α-d-altrose

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β-d-Altrose

The mol-ecule of the title compound, C(6)H(12)O(6), [systematic name: (2R,3S,4R,5R,6R)-6-(hydroxy-meth-yl)oxane-2,3,4,5-tetrol] adopts a (4)C(1) chair conformation with the anomeric hydroxyl group in the equatorial position. All hydroxyl groups act as donors and acceptors in hydrogen bonding and the mol-ecule is involved in ten inter-molecular O-H⋯O inter-actions [O⋯O = 2.672 (5)-2.776 (4) Å] w...

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Unexpected formation of complex bridged tetrazoles via intramolecular 1,3-dipolar cycloaddition of 1,2-O-cyanoalkylidene derivatives of 3-azido-3-deoxy-D-allose.

An unexpected and interesting intramolecular side reaction occurred during the attempted synthesis of glycosyl cyanides upon treatment of 1-O-acetyl-3-azido-3-deoxyallose derivatives with TMSCN and different Lewis acids. Exo-1,2-O-cyanoalkylidene derivatives formed by neighboring group participation and attack of cyanide underwent, after Lewis-acid mediated isomerization to the endo-isomer, int...

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ژورنال

عنوان ژورنال: Agricultural and Biological Chemistry

سال: 1969

ISSN: 0002-1369

DOI: 10.1080/00021369.1969.10859314