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2005
Carbohydrates
U 0500
2-C-Branched Glycosides from 2'-Carbonylalkyl 2-O-Ms(Ts)-Glycosides. A TanSN2—SN2 Reaction via 1,2-Cyclopropanated Sugars. — An alternative meth04- 202 dem
od for the synthesis of 2-C-branched glycosides with exclusive β-anomeric selection is
presented. Substrates (I) and (IV) react with various nucleophiles under basic conditions. The corresponding 2'-ketone derivative (IX) reacts only with thiols to give the
expected target compounds (XI). The reaction in methanol leads to a stable 1,2-cyclopropanated sugar, proposed to be the intermediate type in all reactions. — (SHAO,
H.; EKTHAWATCHAI, S.; WU, S.-H.; ZOU*, W.; Org. Lett. 6 (2004) 20, 3497-3499;
Inst. Biol. Sci., Natl. Res. Counc. Can., Ottawa, Ont. K1A 0R6, Can.; Eng.) —
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