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Clues from Crystal Structures Pave the Way to Access Chiral myo-Inositol Derived Versatile Synthons: Resolution of Racemic 4-O-Allyl-myo-Inositol-1,3,5-Orthoesters via Corresponding Dicamphanates by Crystallization
Crystal Growth & Design ( IF 3.8 ) Pub Date : 2017-09-07 00:00:00 , DOI: 10.1021/acs.cgd.7b00895
Nivedita T. Patil 1 , Mysore S. Shashidhar 1 , Majid I. Tamboli , Rajesh G. Gonnade 1
Affiliation  

Racemic 4-O-allyl-myo-inositol-1,3,5-orthoesters were resolved as the corresponding diastereomeric dicamphanates by crystallization from alcoholic solvents. Crystals of the two diastereomers of myo-inositol orthoacetate and one diastereomer each of myo-inositol orthoformate and myo-inositol orthobenzoate were obtained in >99% purity, on gram scale. The configuration of all these diastereomers was established by conversion to known chiral myo-inositol derivatives as well as by single crystal structure analysis. It is interesting to note that the procedures for the separation of diastereomeric myo-inositol orthoesters could be evolved due to the knowledge of crystal growth and crystal structures of inositol derivatives of comparable molecular structures. Due to the synthetic versatility of myo-inositol orthoesters, the methods described provide rapid and convenient access to a variety of chiral inositol derivatives with high synthetic potential.

中文翻译:

来自晶体结构的线索为通过手性结晶通过相应的双樟酸酯拆分手性肌醇-肌醇衍生的多功能合成子铺平了道路:消旋4 - O-烯丙基-肌醇-肌醇-1,3,5-原酸酯的消旋

外消旋的4 - O-烯丙基-肌醇-1,3,5-原酸酯通过从醇类溶剂中结晶而拆分为相应的非对映体二樟酸酯。的两种非对映的晶体肌醇肌醇原乙酸酯和一种非对映体的各个肌肉肌醇原甲酸酯和肌醇肌醇orthobenzoate在> 99%的纯度获得,在克规模。所有这些非对映体的构型通过转化成已知的手性建立肌肉肌醇衍生物以及由单一晶体结构分析。有趣的是,非对映体的分离程序肌醇原酸酯可能会进化,这是由于具有可比分子结构的肌醇衍生物的晶体生长和晶体结构的知识。由于合成的多功能性肌醇原酸酯,所述方法描述提供于各种具有高合成潜在的手性肌醇衍生物的快速和方便的访问。
更新日期:2017-09-07
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