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Synthesis 1995; 1995(11): 1383-1388
DOI: 10.1055/s-1995-4110
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Trimethylene Dithioacetals of Carbohydrates; Part 2: D-Arabinose, D-Glucose and D-Mannose 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, Fax +49(251)839772
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Publication Date:
31 December 2000 (online)

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The synthesis of trimethylene dithioacetals of D-arabinose, D-glucose and D-mannose and their isopropylidenation is described. Formation of mono- and diisopropylidene derivatives takes place in moderate to good yields, dependent of the reaction system and the reaction conditions (kinetic and thermodynamic control, respectively). The tendencies for the formation of the individual isopropylidenation pattern are summarized and discussed mainly on the basis of geometric arguments.

carbohydrates - D-arabinose - D-glucose - D-mannose - isopropylidenation - 1,3-dithiane

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