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Branched-chain Sugars, XXIV. - Syntheses of Chain-extended and Branched-chain Sugars by Reactions with 4,5-Dihydro-2-lithio-5-methyl-1,3,5-dithiazine
Paulsen, Hans,Stubbe, Mathias,Heiker, Fred R.
, p. 825 - 837 (2007/10/02)
The synthesis of chain-extended sugars can be achieved by reaction of 4,5-dihydro-2-lithio-5-methyl-1,3,5-dithiazine with carbohydrates containing a primary halogen or a terminal epoxide ring.The desulfurization of these products proceeds under milder conditions than with the corresponding 1,3-dithiane adducts.Heptoses 10, 15, and 30 are obtained by this method.Sugars containing a secondary halogen form elimination products on reaction with 2. - The anion 2 seems to be slightly more reactive than 2-lithio-1,3-dithiane.
