Murakami Teiichi, Sato Yukari, Yoshioka Kyoko, Tanaka Mutsuo
Health Research Institute, National Institute of Advanced Industrial Science and Technology (AIST) Tsukuba Central 6, Tsukuba, Ibaraki 305-8566, Japan.
Research Institute for Energy Conservation, National Institute of Advanced Industrial Science and Technology (AIST) Tsukuba Central 2, Tsukuba, Ibaraki 305-8562, Japan.
Carbohydr Res. 2016 Nov 3;434:121-131. doi: 10.1016/j.carres.2016.09.001. Epub 2016 Sep 4.
A regio- and stereo-controlled, rhodium(II)-catalyzed amidoglycosylation of alcohols has been developed using O-acetylated glycals, trichloroethoxysulfonamide, and iodosobenzene. This one-pot amidoglycosylation was applied to a variety of primary and secondary alcohols to afford the β-O-glycosides with acceptable yields up to 84%. The reaction would proceed via stereoselective intermolecular aziridination of the glycal from the α-face followed by S2 reaction with alcohol at C-1 from the β-face to give 1,2:2,3-di-trans-substituted isomer only.
利用O-乙酰化糖烯、三氯乙氧基磺酰胺和亚碘酰苯，开发了一种区域和立体控制的铑（II）催化的醇的氨糖基化反应。这种一锅法氨糖基化反应适用于多种伯醇和仲醇，以高达84%的可接受产率得到β-O-糖苷。该反应将通过糖烯从α面的立体选择性分子间氮杂环丙烷化，然后在C-1处从β面与醇进行S2反应，仅生成1,2:2,3-二反式取代的异构体。
