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Synthesis 1988; 1988(5): 373-375
DOI: 10.1055/s-1988-27577
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(2S,3R)-2-Benzyloxy-3,4-epoxybutan-1-ol, A Versatile Synthetic Building Block Formally Derived From (u)-Tartaric acid

Geo Adam* , Dieter Seebach
  • *Laboratorium für organische Chemie der Eidgenössischen Technischen Hochschule, ETH-Zentrum, Universitätstraße 16, CH-8092 Zürich, Switzerland
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Publikationsdatum:
20. August 2002 (online)

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The title chiral C4-building block2 1, a meso-tartaric acid synthon, is prepared from dimethyl (R,R)-O,O′-benzylidenetartrate on a multigram scale. The key step is a tosylation- reduction sequence which leads to the diol 5.