Stereoselective C-glycosidation of d-fucose derivatives directed by the protective groups
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- 作者：Omar Cortezano-Arellanoa ; &dagger ; ; Camilo A. Melé ; ndez-Becerraa ; Fernando Corté ; sb ; Fernando Sartillo-Piscilc ; Alejandro Cordero-Vargasa ; acordero@unam.mx" class="auth_mail
- 关键词：Carbohydrates ; Stereoselectivity ; Lactones ; Fucose derivatives
- 刊名：Carbohydrate Research
- 出版年：1 July 2014
- 年：2014
- 卷：393
- 期：Complete
- 页码：51-59
- 全文大小：2273 K
文摘
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Stereoselectivity for the reduction of the lactols can be modulated by the correct choice of protective groups.
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Lactols possessing TBDMS protective groups afford the 伪-anomer, whereas their benzylated congeners provide the 尾-anomer.
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This change in stereoselectivity is observed in carbohydrate derivatives possessing 2,3-trans substituents.
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The phenomenon is observed only when the C2 and C3 protective groups are the same (both benzyl or both TBDMS).