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Synlett 1996; 1996(8): 772-774
DOI: 10.1055/s-1996-5513
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Addition of Silyl- and Stannyl Anions to Carbohydrate-Derived 2,3-Dihydro-4H-pyran-4-ones: Facile Access to Glycosyl Silanes and -Stannanes

Andreas Kirschning* , Jan Harders
  • *Institut für Organische Chemie der Technischen Universität Clausthal, Leibnizstraße 6, D-38678 Clausthal-Zellerfeld, Germany, FAX: int. (+)-(0)5323-72 2858; e-mail: andreas.kirschning@tu-clausthal.de
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Publication History

Publication Date:
31 December 2000 (online)

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Conjugate addition of silyl cuprates 1a,b and lithio trialkyl stannanes 1c,d to monosaccharide-derived 2,3-dihydro-4H-pyran-4-ones 2-5 and 10 constitutes a new entry to silyl- and stannyl glycosides 6-9 and 11-13 which either may be employed for the Sila-Baeyer-Villiger oxidation to give pyranoses or are potential precursors for C-glycosides. The keto functionality in 8a/13a can efficiently be reduced to the alcohol in 14a or methylated to form 15 without affecting the anomeric silyl- or stannyl group.

conjugate addition - 2,3-dihydro-4H-pyran-4-ones - glycosyl silanes - glycosyl stannanes

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