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Dual course of bisacetonation of D-xylose in a system Me2CO-Me2C(OMe)2-H2SO4
Authors:L. S. Khasanova  N. K. Selezneva  F. A. Gimalova  M. S. Miftakhov
Affiliation:(1) Institute of Organic Chemistry, Ufa Scientific Center, Russian Academy of Sciences, Ufa, 450054, Russia
Abstract:In the course of formation of a bisisopropylidene protective group by keeping D-xylose in a mixture Me2CO-(MeO)2CMe2-H2SO4 alongside the expected 1,2:4,5-O-diisopropylidene derivative formed minor dimethylacetal, 2,3:4,5-O-diisopropylidene-D-xylose, inseparable from the main product by the chromatography on SiO2. The conditions were found for the selective formation and isolation of the latter, some its one-pot transformations were studied resulting in synthetically promising orthogonally protected acyclic C5-synthons.
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