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

doi:10.1055/s-1996-4320

Synthesis 1996; 1996(8): 963-969
DOI: 10.1055/s-1996-4320

paper

© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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

Abstract

PDF Download All articles of this category

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

PDF (607 kb)