An improved synthesis of latanoprost involving effective control on 15(S) diastereomer

Sachin A. Sasane; Nandu B. Bhise; Girij P. Singh; Alex Joseph; Gautham G. Shenoy

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An improved synthesis of latanoprost involving effective control on 15(S) diastereomer

机译：改进的Latanoproprost合成涉及有效控制的15（S）非对映异构体

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An improved process for the synthesis of latanoprost having excellent optical purity (de 99.9%, [α]D~(20)=+35.37~° (c=0.90, acetonitrile)) without use of preparative HPLC is described. This process involves effective purification of hydroxyl intermediate (5A) through solvent crystallization followed by inhibition of inversion of the chiral center at C-15 position. This was possible due to judicious use of diol intermediate (6) for double bond reduction prior to hydroxyl protection.

机译：描述了一种改进的Latanoproprost的方法，具有优异的光学纯度（DE 99.9％，[α] D〜（20）= + 35.37〜°（C = 0.90，乙腈），无需使用制备型HPLC。该方法涉及通过溶剂结晶有效纯化羟基中间体（5a），然后抑制C-15位置的手性中心的转化。由于在羟基保护之前的双键减少的二醇中间体（6），这是可能的。

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来源
《Synthetic Communications》 |2019年第20期|共7页
作者
Sachin A. Sasane; Nandu B. Bhise; Girij P. Singh; Alex Joseph; Gautham G. Shenoy;
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作者单位

Chemical Research and Development Lupin Ltd Mulshi Pune India;

Chemical Research and Development Lupin Ltd Mulshi Pune India;

Chemical Research and Development Lupin Ltd Mulshi Pune India;

Department of Chemistry Manipal Academy of Higher Education Manipal India;

Department of Chemistry Manipal Academy of Higher Education Manipal India;

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原文格式 PDF
正文语种 eng
中图分类有机化学;
关键词
Crystallization; diol intermediate; ketone intermediate; latanoprost; p-nitrobenzoyl chloride; preparative HPLC;

机译：结晶;二醇中间体;酮中间体;Latanoproprod;p-硝基苯甲酰氯;制备型HPLC;

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1. An improved synthesis of latanoprost involving effective control on 15(S) diastereomer [J] . Sachin A. Sasane, Nandu B. Bhise, Girij P. Singh, Synthetic Communications . 2019,第17a20期

机译：改进的Latanoproprost合成涉及有效控制的15（S）非对映异构体
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An improved synthesis of latanoprost involving effective control on 15(S) diastereomer

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