A novel β-directing fructofuranosyl donor concept. Stereospecific synthesis of sucrose

S Oscarson, FW Sehgelmeble

Index: Oscarson; Sehgelmeble Journal of the American Chemical Society, 2000 , vol. 122, # 37 p. 8869 - 8872

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Citation Number: 35

Abstract

A new concept for the construction of β-d-fructofuranosides based on the idea of locking the anomeric CH2OH group to the α-side through an internal bridge to the 4-hydroxyl group is presented. Thioglycoside fructose donors containing an internal 1, 4-O-(1, 1, 3, 3- tetraisopropyldisiloxane-1, 3-diyl)(TIPS) acetal bridge have been constructed and used in glycosylations with dimethyl (thiomethyl) sulfonium triflate (DMTST) as promoter. The ...