On the stereochemistry of aryl C-glycosides: Unusual behavior of bis-TBDPS protected aryl C-olivosides
On the stereochemistry of aryl C-glycosides: Unusual behavior of bis-TBDPS protected aryl C-olivosides
复制标题
DOI：
10.1016/0040-4039(95)02227-9
复制
发表时间：
1996-01-29
影响因子：
1.8
通讯作者：
Suzuki, K
中科院分区：
文献类型：
--
作者：
Hosoya, T;Ohashi, Y;Suzuki, K
D-橄榄糖基供体的C（3）和C（4）羟基均被一个非常大的基团t-BuPh（2）Si保护，以α-选择性方式进行芳基C-糖苷化，产物构型在各种刘易斯酸条件下保持不变。这些特征通过糖基供体和C-糖苷产物中吡喃糖苷环（C-1（4））的环翻转来合理化，这是由于甲硅烷氧基的严重排斥。
A D-olivosyl donor in which the C(3) and C(4) hydroxyls are both protected by an extremely bulky group, t-BuPh(2)Si, undergoes aryl C-glycosidation in an alpha-selective manner, and the product configuration remains unchanged under various Lewis acid conditions. The features are rationalized by the ring flipping of the pyranoside ring (C-1(4)) in the glycosyl donor and the C-glycoside product, due to the severe repulsion of the siloxy groups.