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Synthesis of Medium and Large Ring Compounds, XLI Synthesis and Reactions of Optically Active Bridged Methyl Deoxyfuranosides

✍ Scribed by Tochtermann, Werner ;Mattauch, Anne-Katrin ;Kasch, Michael ;Peters, Eva-Maria ;Peters, Karl ;von Schnering, Hans Georg

Publisher
John Wiley and Sons
Year
2006
Tongue
English
Weight
678 KB
Volume
1996
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

The resolution of the earlier reported racemic bridged methyl deoxyfuranosides 1 and 3 was achieved via fractional crystallization of the ephedrinium salts 2 or by column chromatography of the camphanoates 5. The absolute configurations of 1 and 3 were established by X‐ray structural analysis of the (S)‐α‐naphthylethylammonium carboxylate (+)‐4 and by correlation with the other enantiomerically pure compounds of this type. (+)‐3 was converted into the 2,5‐bridged altrose derivative (+)‐8.

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