A novel photochemical synthesis of dideoxyfuranosyl disaccharides

A photochemical glycosylation is described using the chiral cyclobutanone 1. Irradiation of ketone 1 in the presence of monosaccharides 2 and 3 gives photoadducts derived from OH insertion of the transient carbene. The carbene inserts into the N H group in the case of nucleoside 4. Photoinsertion of...

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Bibliographic Details
Published in:Tetrahedron letters 1998-11, Vol.39 (48), p.8783-8786
Main Authors: Angelini, Mark P., Lee-Ruff, Edward
Format: Article
Language:English
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Summary:A photochemical glycosylation is described using the chiral cyclobutanone 1. Irradiation of ketone 1 in the presence of monosaccharides 2 and 3 gives photoadducts derived from OH insertion of the transient carbene. The carbene inserts into the N H group in the case of nucleoside 4. Photoinsertion of the oxacarbene derived from a chiral cyclobutanone with monosaccharides containing one or more free hydroxyl groups gives disaccharides. [Display omitted]
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(98)02015-2