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

Tochtermann Werner | Zendy; Mattauch AnneKatrin | Zendy; Kasch Michael | Zendy; Peters EvaMaria | Zendy; Peters Karl | Zendy; von Schnering Hans Georg | Zendy

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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 .

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