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Synthesis 1995; 1995(11): 1376-1382
DOI: 10.1055/s-1995-4109
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Trimethylene Dithioacetals of Carbohydrates; Part 1: D-Ribose, D-Allose and D-Altrose 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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Publikationsdatum:
31. Dezember 2000 (online)

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The synthesis of trimethylene dithioacetals of D-ribose, D-allose and D-altrose and their isopropylidenation is described. In the latter reaction, fundamental differences are found depending on the reaction system and the reaction conditions. Monoisopropylidene compounds are obtained by a kinetically controlled reaction (acetone or 2-methoxypropene, acid, and short reaction time) or by a thermodynamically controlled reaction in acetone/water. Diisopropylidene derivatives are formed using acetone and 2-methoxypropene, acid, and longer reaction time. The structures are assigned by 1H and 13C NMR spectroscopy.

carbohydrates - D-ribose - D-allose - D-altrose - isopropylidenation - 1,3-dithiane