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Synthesis of modified oligosaccharide derivatives by Ferrier rearrangement

Wieczorek E., Thiem J.

Polish Journal of Chemistry

1999

vol. 73 nr 7

1111-1121

Various glycols of the hexose and pentose series and different dideoxy hexopyranosides undergo smooth (Lewis) acid -catalyzed allylic rearrangement reactions to regioisometric deoxygenated disaccharide derivatives. The corresponding saturated components were obtained by hydrogenation. In addition, yhe neutral version of the Ferrier reaction employing pentenoyl glucal was tested, which gave rearrangement and addition products. Finally, certain glycols were condensed with differently functionalized glycols as aglyconic components to form disaccharide glycals.