化学
糖基化
多糖
一锅法合成
化学合成
试剂
立体化学
模块化设计
组合化学
生物化学
有机化学
催化作用
体外
计算机科学
操作系统
作者
Yunqin Zhang,Zixi Chen,Yingying Huang,Shaojun He,Xingkuan Yang,Zhibing Wu,Xiufang Wang,Guozhi Xiao
标识
DOI:10.1002/anie.202000992
摘要
Abstract The synthesis of long, branched, and complex carbohydrate sequences remains a challenging task in chemical synthesis. Reported here is an efficient and modular one‐pot synthesis of a nona‐decasaccharide and shorter sequences from Psidium guajava polysaccharides, which have the potent α‐glucosidase inhibitory activity. The synthetic strategy features: 1) several one‐pot glycosylation reactions on the basis of N ‐phenyltrifluoroacetimidate (PTFAI) and Yu glycosylation to streamline the chemical synthesis of oligosaccharides, 2) the successful and efficient assembly sequences (first O3′, second O5′, final O2′) toward the challenging 2,3,5‐branched Ara f motif, 3) the stereoselective 1,2‐ cis ‐glucosylation by reagent control, and 4) the convergent [6+6+7] one‐pot coupling reaction for the final assembly of the target nona‐decasaccharide. This orthogonal one‐pot glycosylation strategy can streamline the chemical synthesis of long, branched, and complicated carbohydrate chains.
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