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2005
Carbohydrates
U 0500
Stereoselective Synthesis of 4-(N-Mesylamino)-2,3-unsaturated-α-O-glycosides
a New Glycal-Derived Vinyl α-N-(Mesyl)-aziridine. — The title reaction pro33- 238 via
ceeds aziridine (V), generated in situ from (I) in the presence of tBuOK in benzene. The
intermediate reacts with all kinds of alcohols, phenol, cholesterol or sugars affording
α-O-glycosides predominantly. The reactions are highly stereoselective and totally
regioselective. When the alcohols are used as a solvent, the stereoselectivity is lower
than in benzene. — (DI BUSSOLO, V.; ROMANO, M. R.; PINESCHI, M.; CROTTI*,
P.; Org. Lett. 7 (2005) 7, 1299-1302; Dip. Chim. Bioorg. Biofarm., Univ. Pisa,
I-56126 Pisa, Italy; Eng.) — R. Steudel
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