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首页> 外文期刊>Organic process research & development >A Practical Stereoselective Synthesis and Novel Cocrystallizations of an Amphiphatic SGLT-2 Inhibitor
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A Practical Stereoselective Synthesis and Novel Cocrystallizations of an Amphiphatic SGLT-2 Inhibitor

机译：两性SGLT-2抑制剂的实用立体选择性合成和新型共结晶

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摘要

A practical synthesis of the SGLT-2 inhibitor β-C-aryl-D-glucoside (1) has been developed. The route employed 2,3,4,6-tetra-O-trimethlysilyl-D-glucano-1,5-lactone as the key chiral building block, prepared efficiently from the commercially available, inexpensive raw materials, D-gluconolactone and trimethylsilyl chloride. The salient step in the synthesis is the Lewis acid-mediated stereoselective reduction of a methyl C-aryl peracetylated glycoside using a silyl hydride to set the stereochemistry of the crucial anomeric chiral center. Several novel cocrystalline complexes of 1 with L-phenylalanine and L-proline were discovered. Single-crystal structures of these complexes and several synthetic intermediates have been determined. The l-phenylalanine complex was developed and used to purify and isolate the API. All steps were implemented at multikilogram scale.
机译：已经开发了SGLT-2抑制剂β-C-芳基-D-葡萄糖苷（1）的实用合成方法。该路线以2,3,4,6-四-O-三甲基甲硅烷基-D-葡糖醇-1,5-内酯为主要手性构件，由可商购的廉价原料D-葡糖酸内酯和三甲基甲硅烷基氯有效制备。合成中的重要步骤是使用甲硅烷基氢化物设定关键的异头手性中心的立体化学，路易斯酸介导的甲基C-芳基过乙酰化的糖苷的立体选择性还原。发现了几种新的1与L-苯丙氨酸和L-脯氨酸的共晶复合物。这些配合物和几种合成中间体的单晶结构已经确定。开发了1-苯丙氨酸复合物，并用于纯化和分离API。所有步骤均以千克为单位执行。

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