Stereoselektive Hydrid‐Reduktion von Tetronsäurederivaten. Synthese verzweigtkettiger Tetrofuranosen | Zendy

Wyss Heinz | Zendy; Vögeli Ulrich | Zendy; Scheffold Rolf | Zendy

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Stereoselektive Hydrid‐Reduktion von Tetronsäurederivaten. Synthese verzweigtkettiger Tetrofuranosen

Author(s) -

Wyss Heinz,

Vögeli Ulrich,

Scheffold Rolf

Publication year - 1981

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19810640317

Subject(s) - chemistry , stereoselectivity , stereochemistry , hydride , nuclear magnetic resonance spectroscopy , medicinal chemistry , organic chemistry , catalysis , metal

Stereoselective Hydride Reduction of Tetronic Acid Derivatives, Synthesis of Branched‐Chain Tetrofuranoses The 3‐methoxymethyl derivatives of 2‐methyl‐ D , L ‐threofuranose ( 10a ) and 2‐deoxy‐2‐methyl‐ D , L ‐erythrofuranose ( 11a ) are prepared starting from 2‐methyl‐tetronic acid ( 1 ). The key step is the stereoselective reduction of the 3‐oxo‐function of 2‐chloro‐2‐methyl‐3‐oxo‐γ‐butyrolacton ( 2 ) by sodiumborohydride, which proceeds predominantly anti with respect to the C,Cl‐bond. The configuration of the reduction products has been established by 1 H‐ and 13 C‐NMR.‐spectroscopy.

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