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Synthesis 1996; 1996(8): 963-969
DOI: 10.1055/s-1996-4320
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Trimethylene Dithioacetals of Carbohydrates; Part 4: D-Xylose-, D-Idose and L-Gulose Propane-1,3-diyl Dithioacetal and Their Isopropylidene Derivatives

Olaf Kölln, Hartmut Redlich*
  • *Organisch-Chemisches Institut der Westfälischen Wilhelms-Universität Münster, Corrensstraße 40, D-48149 Münster, Germany
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Publication Date:
31 December 2000 (online)

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The synthesis of trimethylene dithioacetals of D-xylose, D-idose- and L-gulose and their isopropylidenation is described. Several mono- and diisopropylidene derivatives are available using various reaction systems and reaction conditions (kinetic and thermodynamic control, respectively). Differences in formation of the individual isopropylidene compounds are discussed mainly on the basis of geometric arguments. The structure are assigned by 1H and 13CNMR spectroscopy.

carbohydrates - D-xylose - D-idose - L-gulose - isopropylidenation - 1,3-dithiane

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