Y(OTf)3 as a highly efficient catalyst in Ferrier Rearrangement for the synthesis of O- and S-2,3-unsaturated glycopyranosides
2014
Chen, Peiran | Li, Shan
By using Y(OTf)3 as the catalyst, a series of 2,3-unsaturated-glucosides have been synthesized from 3,4,6-tri-O-acetyl-d-glucal, 3,4-di-O-acetyl-l-rhamnal, and 3,4,6-tri-O-benzyl-d-glucal under mild reaction conditions in good yields with high anomeric selectivities. It was found that, in this reaction, 3,4,6-tri-O-benzyl-d-glucal behaved differently from the other two glucals when it was reacted with phenol, O-benzyl glucoside instead of O-phenyl glucoside formed as the sole product. An explanation is given for this phenomenon.
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书目信息
出版者
Elsevier Ltd
其它主题
Y(otf)3; 3-unsaturated glycoside; Ferrier rearrangement; 4-di-o-acetyl-l-rhamnal; 6-tri-o-acetyl-d-glucal; 6-tri-o-benzyl-d-glucal
语言
英语
类型
Journal Article; Text
2024-02-28
MODS