Both O-glycosides and nucleosides are essential biomolecules with important roles in a variety of biological processes. Chemical synthesis of both O-glycosides and nucleosides is a scalable and reliable method to develop new therapeutic agents and decipher their functions. However, the efficient synthesis of both O-glycosides and nucleosides remains one of long-standing challenges in chemical synthesis. In particular, ether-type glycosyl donors are rarely developed to achieve the efficient synthesis of both O-glycosides and nucleosides due to the stronger conditions required for breaking of the glycosidic C¨CO bond. Here we report that ortho-(1-phenylvinyl) benzyl glycosides are new ether-type donors for efficient synthesis of both O-glycosides and nucleosides under mild reaction conditions. This glycosylation method enables glycosylation with both alcoholic acceptors and nucleobases with a variety of reactive functionalities. Furthermore, the latent-active synthesis of glycans and the efficient synthesis of nucleosides antibiotics have also been successfully demonstrated in the current glycosylation protocol, thereby representing an important step toward streamlining the chemical synthesis of both O-glycosides and nucleosides.

中文翻译：

---

邻-（1-苯基乙烯基）苄基糖苷：有效合成O-糖苷和核苷的醚型糖基供体

O-糖苷和核苷都是必需的生物分子，在各种生物过程中都起着重要的作用。O-糖苷和核苷的化学合成是开发新治疗剂并破译其功能的可扩展且可靠的方法。然而，O-糖苷和核苷的有效合成仍然是化学合成中长期存在的挑战之一。特别地，由于破坏糖苷C–CO键所需的更强条件，很少开发醚型糖基供体来实现O-糖苷和核苷的有效合成。在这里我们报道邻-（1-苯基乙烯基）苄基糖苷是在温和的反应条件下有效合成O-糖苷和核苷的新型醚型供体。这种糖基化方法使得能够与具有多种反应性官能团的醇受体和核碱基进行糖基化。此外，聚糖的潜在活性合成和核苷抗生素的有效合成也已在当前的糖基化方案中得到成功证明，从而代表了简化O-糖苷和核苷化学合成的重要一步。