Stereoselective synthesis of 3-deoxy-piperidine iminosugars from l-lysine
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概要
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A new method using electrochemical oxidation and/or OsO4 oxidation has been used for the stereoselective synthesis of 2,3,6-trihydroxylated (5S)-piperidine derivatives. The electrochemical method was successively used for the conversion of N-protected piperidines to N-protected 1-methoxypiperidines and for the conversion of 2,3-didehydro-1-methoxypiperidine derivatives to 2,3-trans-1,2,3-triacetoxypiperidine derivatives. These triacetates were easily transformed into (2S,3S)-6-triacetoxy-(5S)-methylpiperidine and (2R,3R)-6-triacetoxy-(5S)-methylpiperidine. In addition, the 2,3-cis-dihydroxylation of 2,3-didehydro-1-methoxypiperidine derivatives with OsO4 afforded (2R,3S)-6-triacetoxy-(5S)-methylpiperidine and (2S,3R)-6-triacetoxy-(5S)-methylpiperidine.
- Elsevier Ltd.の論文
- 2009-12-11
著者
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Onomura Osamu
Graduate School Of Biomedical Sciences Nagasaki Univ. 1-14 Bunkyo-machi Nagasaki 852-8521 Jpn
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Matsumura Yoshihiro
Graduate School Of Biomedical Sciences Nagasaki Univ. 1-14 Bunkyo-machi Nagasaki 852-8521 Jpn
関連論文
- Palladium-imidazolinium carbene-catalyzed arylation of aldehydes with arylboronic acids in water
- Regioselective Introduction of Electrophiles into Piperidine Derivatives at the 4-Position
- Facile synthesis of optically active oxindoles by copper-catalyzed asymmetric monotosylation of prochiral 1,3-diols
- Stereoselective synthesis of 3-deoxy-piperidine iminosugars from l-lysine
- Ring Contraction of α,β-Unsaturated Cyclic Amines with cis-Dihydroxylation at the α,β-Position
- Electrochemical Oxidation of 1,2-Diols to α-Hydroxyketones in Water