Protecting-group- and microwave-free synthesis of β-glycosyl esters and aryl β-glycosides of N-acetyl-d-glucosamine
Protecting-group- and microwave-free synthesis of β-glycosyl esters and aryl β-glycosides of N-acetyl-d-glucosamine
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N-乙酰基-d-葡萄糖胺的β-糖基酯和芳基β-糖苷的无保护基团和微波合成
DOI：
10.1016/j.bmc.2022.116852
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发表时间：
2022
期刊：
影响因子：
--
通讯作者：
Tanaka Hide-Nori
中科院分区：
文献类型：
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作者：
Hamaya Yu;Komura Naoko;Imamura Akihiro;Ishida Hideharu;Ando Hiromune;Tanaka Hide-Nori
利用N-乙酰基-D-氨基葡萄糖（GlcNAc）恶唑啉的潜在化学反应活性，提出了一种无保护基合成β-糖基酯和芳基β-糖苷的方法。GlcNAc恶唑啉在不使用催化剂或加热条件下（即，微波辐射），以中等至优异的产率和β-选择性提供所需产物。这种简单的无保护基团的方法表现出广泛的底物范围和良好的官能团耐受性，并且它允许有效地生产一类新型的GlcNAc缀合的生物材料和前药候选物。
A protecting-group-free method for synthesis of β-glycosyl esters and aryl β-glycosides was developed by using latent chemical reactivity ofN-acetyl-d-glucosamine (GlcNAc) oxazoline. The GlcNAc oxazoline was spontaneously reacted with carboxylic acids and phenol derivatives via the oxazoline ring opening without the use of a catalyst or heating conditions (i.e., microwave irradiation), affording the desired products in moderate to excellent yields with β-selectivity. This simple protecting-group-free method exhibits a wide substrate scope and good functional group tolerance, and it allows the efficient production of a novel class of GlcNAc-conjugated biomaterials and prodrug candidates.