Enantiomeric Resolution and Absolute Stereochemistry of Stable Rotamers of Dimethyl 6,6'-Dimethyl-9,9'-bitriptycyl-2,2'-dicarboxylate as a Stereochemical Analog of(R*,R*)-and(R,S)-Tartaric Acids

Shinji Toyota; Akinori Takau; Yo Hitaka; Michinorioki; Kan Wakamatsu

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Enantiomeric Resolution and Absolute Stereochemistry of Stable Rotamers of Dimethyl 6,6'-Dimethyl-9,9'-bitriptycyl-2,2'-dicarboxylate as a Stereochemical Analog of(R,R)-and(R,S)-Tartaric Acids

机译：（R *，R *）-和（R，S）-的立体化学类似物的6,6'-二甲基-9,9'-bitriptycyl-2,2'-二羧酸二甲酯的稳定旋转异构体的对映体拆分和绝对立体化学。酒石酸

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The title 9,9'-bitriptycyl compound,regarded as a Stereochemical analogue of tartaric acid,possesses a total of five diastereomers,among which two rotamers belonging to the(R*,R*)form were isolated by chromatographic separation.Their relative stereochemistries were determined by X-ray analysis to be ap-(R*,R*)and sc*-(R*,R*).The enantiomers of these isomers were resolved by chiral HPLC and found to be optically and CD active.To predict the absolute stereochemistry,the CD spectra were calculated by the TDDFT method for the two rotamers as well as the chiral(R,S)form.The spectral pattern depends on the absolute arrangement of the two COOMe substituted benzeno groups,leading to the assignment of ap-(S,S),Psc-(R,R),and Msc-(R,S)for the(-)-forms.Since the achiral ap-(R,S)form was already known,we established the Stereochemical relationship of all of the possible isomers of the tartaric acid-type molecule except for a pair of enantiomers of one missing isomer,the sc*-(S*,S*)form.

机译：标题9,9'-Bitriptycylyl化合物，作为酒石酸的立体化学类似物，具有五个非对映异构体，其中两个（R *，R *）异构体通过色谱分离得到。其相对立体化学通过X射线分析确定为ap-（R *，R *）和sc *-（R *，R *）。通过手性HPLC拆分这些异构体的对映异构体，发现它们具有光学和CD活性。预测绝对立体化学，通过TDDFT方法计算两个旋转异构体以及手性（R，S）形式的CD光谱。光谱模式取决于两个COOMe取代的苯甲烯基团的绝对排列，导致分配（-）形式的ap-（S，S），Psc-（R，R）和Msc-（R，S）的关系。由于已知非手性ap-（R，S）形式酒石酸型分子的所有可能异构体的立体化学关系，除了一对缺少一种异构体的对映体（sc *-（S *，S *）形式）。

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《Bulletin of the Chemical Society of Japan》 |2005年第12期|共7页
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Shinji Toyota; Akinori Takau; Yo Hitaka; Michinorioki; Kan Wakamatsu;
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1. Enantiomeric Resolution and Absolute Stereochemistry of Stable Rotamers of Dimethyl 6,6'-Dimethyl-9,9'-bitriptycyl-2,2'-dicarboxylate as a Stereochemical Analog of(R*,R*)-and(R,S)-Tartaric Acids [J] . Shinji Toyota, Akinori Takau, Yo Hitaka, Bulletin of the Chemical Society of Japan . 2005,第12期

机译：（R *，R *）-和（R，S）-的立体化学类似物的6,6'-二甲基-9,9'-bitriptycyl-2,2'-二羧酸二甲酯的稳定旋转异构体的对映体拆分和绝对立体化学。酒石酸
2. Cu(I)-Based Sensitizers Featuring 6,6 '-Dimethyl-4,4 '-Dicarboxylate-2,2 '-Bipyridine with Functionalized 2,9-Dimethyl-1, 10-Phenanthroline Ligands: A Structural, Electronic and Spectral Investigation [J] . Wei Shuxian, Shi Xiaofan, Lu Xiaoqing, Science of advanced materials . 2015,第7期

机译：具有功能化的2,9-二甲基-1，10-菲咯啉配体的6,6'-二甲基-4,4'-二羧酸-2,2'-联吡啶的基于Cu（I）的敏化剂：结构，电子和光谱研究
3. Structures and inclusion properties of racemic and enantiopure dimethyl and diphenyl 9,9'-bianthryl-2,2-dicarboxylates [J] . Toyota S, Shimasaki T, Hirano S, Chirality: The pharmacological, biological, and chemical consequences of molecular asymmetry . 2008,第3a4期

机译：外消旋和对映体纯的二甲基和二苯基9,9'-二蒽基-2,2-二羧酸酯的结构和包合性质
4. STUDIES IN STEREOCHEMISTRY. PART I: SYNTHESIS, RESOLUTION AND ABSOLUTE CONFIGURATION OF (E)-2,4-DIMETHYL-2-HEXENOIC ACID. PART II: THE DETERMINATION OF THE HEAT OF HYDROGENATION AND REARRANGEMENT BEHAVIOR OF 1,1'-SPIROBIINDENE. PART III: SYNTHESIS AND CHIROPTICAL PROPERTIES OF 5,7-DIOXOBICYCLO(2.2.2)OCT-2-ENE AND BICYCLO(2.2.2)OCTAN-2,5-DIONE. [D] . MORTON, GERALD HUNT. 1980

机译：立体化学研究。第一部分：（E）-2,4-二甲基-2-己酸的合成，拆分和绝对构型。第二部分：1,1'-螺双茚的加氢热和重排行为的测定。第三部分：5,7-二氧杂双环（2.2.2）OCT-2-烯和双环（2.2.2）OCTAN-2,5-二酮的合成和手性。
5. Efficient Optical Resolution of 2,2′-Dihydroxy-1,1′-binaphthyl and 10,10′-Dihydroxy-9,9′-biphenanthryl by Complex Formation with Novel Chiral Host Compounds Derived from Tartaric Acid [O] . Fumio Toda, Koichi Tanaka, Luigi Nassimbeni, 1988

机译：通过络合物形成，高效光学分辨率的2,2'-二羟基-1,1'-二苯甲基和10,10'-二羟基-9,9'- Biphenshryl的络合物形成衍生自酒石酸的新型手性宿主化合物

Enantiomeric Resolution and Absolute Stereochemistry of Stable Rotamers of Dimethyl 6,6'-Dimethyl-9,9'-bitriptycyl-2,2'-dicarboxylate as a Stereochemical Analog of(R*,R*)-and(R,S)-Tartaric Acids

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Enantiomeric Resolution and Absolute Stereochemistry of Stable Rotamers of Dimethyl 6,6'-Dimethyl-9,9'-bitriptycyl-2,2'-dicarboxylate as a Stereochemical Analog of(R,R)-and(R,S)-Tartaric Acids