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Dual course of bisacetonation of D-xylose in a system Me2CO-Me2C(OMe)2-H2SO4

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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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Authors and Affiliations

  1. Institute of Organic Chemistry, Ufa Scientific Center, Russian Academy of Sciences, Ufa, 450054, Russia

    L. S. Khasanova, N. K. Selezneva, F. A. Gimalova & M. S. Miftakhov

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  1. L. S. Khasanova
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  2. N. K. Selezneva
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  3. F. A. Gimalova
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  4. M. S. Miftakhov
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Corresponding author

Correspondence to L. S. Khasanova.

Additional information

Original Russian Text © L.S. Khasanova, N.K. Selezneva, F.A. Gimalova, M.S. Miftakhov, 2009, published in Zhurnal Organicheskoi Khimii, 2009, Vol. 45, No. 5, pp. 775–778.

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Khasanova, L.S., Selezneva, N.K., Gimalova, F.A. et al. Dual course of bisacetonation of D-xylose in a system Me2CO-Me2C(OMe)2-H2SO4 . Russ J Org Chem 45, 762–765 (2009). https://doi.org/10.1134/S1070428009050194

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  • DOI: https://doi.org/10.1134/S1070428009050194

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