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Synthesis of Medium and Large Ring Compounds, XLI Synthesis and Reactions of Optically Active Bridged Methyl Deoxyfuranosides
Author(s) -
Tochtermann Werner,
Mattauch AnneKatrin,
Kasch Michael,
Peters EvaMaria,
Peters Karl,
von Schnering Hans Georg
Publication year - 1996
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199619960305
Subject(s) - chemistry , optically active , derivative (finance) , resolution (logic) , ring (chemistry) , fractional crystallization (geology) , crystallization , stereochemistry , organic chemistry , geochemistry , artificial intelligence , basalt , computer science , financial economics , economics , geology
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 .