4,6-二-O-苄基-myo-肌醇和肌醇1,3,5-原酸酯的简便合成

Convenient synthesis of 4,6-di-O-benzyl-myo-inositol and myo-inositol 1,3,5-orthoesters.

作者信息

Praveen T, Shashidhar M S

机构信息

Division of Organic Synthesis, National Chemical Laboratory, Pune, India.

出版信息

Carbohydr Res. 2001 Feb 15;330(3):409-11. doi: 10.1016/s0008-6215(00)00296-2.

DOI:10.1016/s0008-6215(00)00296-2

PMID:11270820

Abstract

Convenient high yielding methods for the preparation of 4,6-di-O-benzyl-myo-inositol, myo-inositol 1,3,5-orthoformate and myo-inositol 1,3,5-orthoacetate, without involving chromatography are described. Myo-inositol was converted to racemic 2,4-di-O-benzoyl-myo-inositol 1,3,5-orthoformate by successive treatment with triethyl orthoformate and benzoyl chloride. The dibenzoate obtained on benzylation with benzyl bromide and silver(I) oxide gave 2-O-benzoyl-4,6-di-O-benzyl-myo-inositol 1,3,5-orthoformate. Deprotection of the benzoate and the orthoformate with isobutylamine and aqueous trifluoroacetic acid, respectively gave 4,6-di-O-benzyl-myo-inositol in an overall yield of 67%. Myo-inositol orthoformate and orthoacetate were prepared and isolated as their tribenzoates. The free orthoesters were regenerated by deprotection of the benzoates by aminolysis with isobutylamine.

摘要

本文描述了不涉及色谱法的制备4,6-二-O-苄基-myo-肌醇、肌醇1,3,5-原甲酸酯和肌醇1,3,5-原乙酸酯的简便高产方法。通过依次用原甲酸三乙酯和苯甲酰氯处理，将肌醇转化为外消旋的2,4-二-O-苯甲酰基-myo-肌醇1,3,5-原甲酸酯。用苄基溴和氧化银（I）进行苄基化反应得到的二苯甲酸酯生成了2-O-苯甲酰基-4,6-二-O-苄基-myo-肌醇1,3,5-原甲酸酯。分别用异丁胺和三氟乙酸水溶液对苯甲酸酯和原甲酸酯进行脱保护，得到4,6-二-O-苄基-myo-肌醇，总收率为67%。肌醇原甲酸酯和原乙酸酯以其三苯甲酸酯的形式制备和分离。通过用异丁胺进行氨解对苯甲酸酯进行脱保护，从而再生游离的原酸酯。