Evolution of a Reagent-Controlled Strategy for β-Selective C-Glycoside Synthesis
Evolution of a Reagent-Controlled Strategy for β-Selective C-Glycoside Synthesis
复制标题
β-选择性 C-糖苷合成的试剂控制策略的演变
DOI：
10.1055/a-1755-3090
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发表时间：
2022
期刊：
影响因子：
2
通讯作者：
Bennett, Clay S.
中科院分区：
文献类型：
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作者：
Bennett, Clay S.
c -烷基糖苷是一类极具吸引力的非水解碳水化合物模拟物，作为下一代治疗药物具有巨大的潜力。然而，直接立体选择性合成具有广泛底物耐受性的c -烷基糖苷的方法有限。特别是在β-连接c -烷基糖苷的情况下，从常见的偶联伙伴直接合成的方法仍然有限。本报告描述了我们实验室对糖基磺酸盐化学研究的演变，从构建简单的β-连接的2-脱氧糖的方法到直接合成β-连接的酰基和纯酰基糖苷的技术，这些糖苷可以被加工成更复杂的结构2糖基磺酸盐；3糖基磺酸盐在低聚糖合成中的应用；4供体与磺酸盐的匹配反应；5 β-连接的c -酰基和纯酰基糖苷的合成；6对其他产品的精制；7结论
C-Alkyl glycosides represent an attractive class of nonhydrolyzable carbohydrate mimetics which possess enormous potential as next-generation therapeutics. Methods for the direct stereoselective synthesis ofC-alkyl glycosides with a broad substrate tolerance are limited, however. This is especially in the case of β-linkedC-alkyl glycosides, where direct methods for synthesis from commonly available coupling partners remain limited. This Account describes the evolution of our laboratory’s studies on glycosyl sulfonate chemistry from a method for the construction of simple β-linked 2-deoxy-sugars to a technology for the direct synthesis of β-linked acyl and homoacyl glycosides that can be elaborated into more complex structures.1 Introduction2 Glycosyl Sulfonates3 Glycosyl Sulfonates in Oligosaccharide Synthesis4 Matching Donor and Sulfonate Reactivity5 β-LinkedC-Acyl and Homoacyl Glycoside Synthesis6 Elaboration to other Products7 Conclusion