S-Benzoxazolyl as a stable protecting moiety and a potent anomeric leaving group in oligosaccharide synthesis
S-Benzoxazolyl as a stable protecting moiety and a potent anomeric leaving group in oligosaccharide synthesis
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DOI：
10.1021/jo071191s
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发表时间：
2007-08-31
影响因子：
3.6
通讯作者：
Demchenko, Alexei V.
中科院分区：
文献类型：
--
作者：
Kamat, Medha N.;De Meo, Cristina;Demchenko, Alexei V.
作为开发用于立体选择性糖基化和收敛低聚糖合成的新的通用构建块计划的一部分，我们证明了S-苯并恶唑(Sbox)糖苷对糖化学中主要的保护基团操作是稳定的。另一方面，它们可以在相对温和的反应条件下糖化，得到1，2-反式或1，2-顺式连接的二糖。Sbox部分的选择性和化学选择性激活也被证明是可行的，这是通过合成一些寡糖序列来证明的。
As a part of a program for developing new versatile building blocks for stereoselective glycosylation and convergent oligosaccharide synthesis, we demonstrated that S-benzoxazolyl (SBox) glycosides are stable toward major protecting group manipulations employed in carbohydrate chemistry. On the other hand, they can be glycosidated under relatively mild reaction conditions to afford either 1,2-trans or 1,2-cis-linked disaccharides. Selective and chemoselective activations of the SBox moiety were also proved to be feasible, which was demonstrated by synthesizing a number of oligosaccharide sequences.