Synthesis of Glycoside Derivatives Employing the Ferrier Rearrangement 1 |
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| Authors: | Eusebius Wieczorek Joachim Thiem |
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| Institution: | Institut für Organische Chemie, Universit?t Hamburg , Martin-Luther-King-Platz 6, D-20146, Hamburg, Germany |
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| Abstract: | Abstract Various glycals underwent smooth Lewis acid-catalysed allylic rearrangement reactions with O-nucleophiles to yield 2,3-unsaturated glycoside derivatives. In the hexose series predominantly α-D-, and in the pentose series β-D-anomers resulted. Among others Ω-cyano- as well as Ω-benzyloxycarbonylamino functionalised alcohols could be used successfully. With diols the corresponding 1,1′-bridged disaccharides could be obtained. |
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