Stereoselective Synthesis of 2,3-Unsaturated-aza-O-glycosides via New Diastereoisomeric N-Cbz-imino Glycal-Derived Allyl Epoxides

Stereoselective Synthesis of 2,3-Unsaturated-aza-O-glycosides via New Diastereoisomeric N-Cbz-imino Glycal-Derived Allyl Epoxides

Diastereoisomeric d,l-N-Cbz-imino glycal-derived allyl epoxides 5 and 6 have been synthesized, and their addition reactions with alcohols examined. The reactions lead to the corresponding 2,3-unsaturated-aza-O-glycosides through a new, completely regioselective 1,4-addition process which proceeds wi...

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Veröffentlicht in:Organic letters 2007-10, Vol.9 (22), p.4479-4482
Hauptverfasser: Di Bussolo, Valeria, Fiasella, Annalisa, Romano, Maria Rosaria, Favero, Lucilla, Pineschi, Mauro, Crotti, Paolo
Format: Artikel
Sprache:eng
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Zusammenfassung:Diastereoisomeric d,l-N-Cbz-imino glycal-derived allyl epoxides 5 and 6 have been synthesized, and their addition reactions with alcohols examined. The reactions lead to the corresponding 2,3-unsaturated-aza-O-glycosides through a new, completely regioselective 1,4-addition process which proceeds with complete substrate-dependent stereoselectivity.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol701836a