De Novo Synthetic Approach to 2,4-Diamino-2,4,6-trideoxyhexoses (DATDH): Bacterial and Rare Deoxy-Amino Sugars.
De Novo Synthetic Approach to 2,4-Diamino-2,4,6-trideoxyhexoses (DATDH): Bacterial and Rare Deoxy-Amino Sugars.
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2,4-二氨基-2,4,6-三脱氧己糖 (DATDH) 的从头合成方法：细菌和稀有脱氧氨基糖。
DOI：
10.1021/acs.orglett.3c03106
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发表时间：
2023
期刊：
影响因子：
5.2
通讯作者：
Bennett,ClayS
中科院分区：
文献类型：
--
作者：
Vasquez,Olivea;Alibrandi,Angela;Bennett,ClayS
本文介绍了一条合成2，4-二氨基-2，4，6-三脱氧糖立体异构体的路线，经6-7步反应，总收率22-33%。该途径中的关键步骤是通过手性铱-H8-BINAP介导的d-和l-苏氨醇和l-别-苏氨醇与邻苯二甲酰亚胺-丙二烯的羰基偶联，这允许在一个高度非对映选择性（>20：1 dr）步骤中安装两个新的手性中心。这种方法提供了一个更简洁，非对映选择性，和通用的方法来获得这些脱氧氨基糖比目前可用的。
A synthetic route to 2,4-diamino-2,4,6-trideoxysugar stereoisomers in 6–7 steps and 22–33% overall yield is described. A key step in this pathway is the carbonyl coupling ofd- andl-threoninol ord- andl-allo-threoninol to a phthalimido-allene mediated by chiral iridium-H8-BINAP, which allows for installation of two new chiral centers in one, highly diastereoselective (>20:1 dr) step. This approach provides a more concise, diastereoselective, and versatile method to access these deoxy-amino sugars than is currently available.