New entry for asymmetric deoxyazasugar synthesis: syntheses of deoxymannojirimycin, deoxyaltrojirimycin and deoxygalactostatin

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Koji Asano, Toshikazu Hakogi, Seiji Iwama and Shigeo Katsumura


Abstract

Deoxyazasugars such as deoxymannojirimycin, deoxyaltrojirimycin and deoxygalactostatin were stereoselectively synthesized starting from (R)-(+)-4-methoxycarbonyloxazolidinone via a bicyclic oxazolidinylpiperidine as a common synthetic intermediate.


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