2,3(1),4(6),5,6(4)-penta-O-acetyl-sn-myoinositol | 35427-06-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,3(1),4(6),5,6(4)-penta-O-acetyl-sn-myoinositol
• 英文别名: (-)-2,3,4,5,6-penta-O-acetyl-D-myo-inositol；1,2,4,5,6-penta-O-acetyl-sn-myo-inositol；1,2,4,5,6-penta-O-acetyl-sn-myoinositol；1L-2,3,4,5,6-Penta-O-acetyl-myo-inositol；2,3,4,5,6-Penta-O-acetyl-myo-inosit
• CAS: 35427-06-6
• 化学式: C₁₆H₂₂O₁₁
• 分子量: 390.344
• InChiKey: STEDFOFWVUHEQP-YTQIUSBHSA-N

物化性质

• 沸点：
  436.1±45.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.98
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  151.73
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  2,3(1),4(6),5,6(4)-penta-O-acetyl-sn-myoinositol 在 chromium(VI) oxide 、 2,6-lutidinium perchlorate 作用下， 以 氯苯 为溶剂， 反应 79.0h， 生成 1(3),2,4(6),5,6(4)-penta-O-acetyl-sn-myoinositol
  参考文献：
  名称：

  Sibrikov, Yu. I.; Stepanov, A. E.; Shvets, V. I., Journal of Organic Chemistry USSR (English Translation), 1990, vol. 26, # 5.2, p. 899 - 904

  摘要：

  DOI：
• 作为产物：
  描述：

  1(3),4(6),5,6(4)-tetra-O-acetyl-sn-myoinositol 在 吡啶 、 4 A molecular sieve 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 54.0h， 生成 2,3(1),4(6),5,6(4)-penta-O-acetyl-sn-myoinositol
  参考文献：
  名称：

  Sibrikov, Yu. I.; Stepanov, A. E.; Shvets, V. I., Journal of Organic Chemistry USSR (English Translation), 1986, p. 1089 - 1094

  摘要：

  DOI：

文献信息

• Inositol Biotransformation
  申请人：UNIVERSITY COURT OF THE UNIVERSITY OF ST ANDREWS

  公开号：US20160168607A1

  公开（公告）日：2016-06-16

  Disclosed is a method of preparing pure or substantially pure D-myo-inositol-3-phosphate from glucose-6-phosphate and/or fructose-6-phosphate. The method may also be applied to protected and/or derivative forms of glucose-6-phosphate and/or fructose-6-phosphate so as to form protected/derivative forms of D-myo-inositol-3-phosphate, for use in further chemical reactions. The enzyme D-myo-inositol-3-phosphate synthase (INO1) is contacted with the glucose-6-phosphate and/or fructose-6-phosphate to generate labeled or unlabeled, protected or unprotected D-myo-inositol-3-phosphate, which may be further reacted and/or purified.

  披露了一种从葡萄糖-6-磷酸和/或果糖-6-磷酸制备纯净或基本纯净的D-肌醇-3-磷酸的方法。该方法也可应用于葡萄糖-6-磷酸和/或果糖-6-磷酸的保护形式和/或衍生物形式，以形成D-肌醇-3-磷酸的保护/衍生物形式，用于进一步的化学反应。D-肌醇-3-磷酸合酶（INO1）酶与葡萄糖-6-磷酸和/或果糖-6-磷酸接触，以生成标记的或未标记的、保护的或未保护的D-肌醇-3-磷酸，该磷酸可进一步反应和/或纯化。
• Design and synthesis of biotinylated inositol phosphates relevant to the biotin–avidin techniques
  作者：Kensaku Anraku、Teruhiko Inoue、Kenji Sugimoto、Takashi Morii、Yasuo Mori、Yoshinari Okamoto、Masami Otsuka

  DOI：10.1039/b719938d

  日期：——

  Six bifunctional molecules containing biotin and various inositol phosphates were synthesized. These compounds were designed on the basis of X-ray structures of the complexes of D-myo-inositol 1,4,5-triphosphates (IP3) and phospholipase C δ pleckstrin homology domain (PLCδ PH) considering the application to the biotin–avidin techniques. The building blocks of the inositol moiety were synthesized starting with optically resolved myo-inositol derivatives and assembled to the biotin linker through a phosphate linkage.

  合成了六种含有生物素和各种肌醇磷酸盐的双功能分子。这些化合物的设计基于D-myo-肌醇1,4,5-三磷酸（IP3）与磷脂酶C δ pleckstrin同源域（PLCδ PH）复合物的X射线结构，考虑到生物素-抗生物素技术的应用。肌醇部分的构建块是从光学分解的myo-肌醇衍生物开始合成的，并通过磷酸链接组装到生物素链接器上。
• Synthesis of DL-myo-inositol 1-phosphate and its thiophosphate analogue
  作者：Thomas Metschies、Carsten Schultz、Bernd Jastorff

  DOI：10.1016/s0040-4039(00)80381-0

  日期：1988.1

  A novel method for synthesis of myo-inositol 1-phosphate using phosphorus oxychloride is described an transferred to synthesis of its thiophosphate analogue.

  用于合成的新方法肌醇描述肌醇-1-磷酸使用三氯氧化磷的转移到它的硫代类似物的合成。
• Cyclitols. Part XXIV. Selective acetolysis of myoinositol benzyl ethers
  作者：S. J. Angyal、M. H. Randall、M. E. Tate

  DOI：10.1039/j39670000919

  日期：——

  The acetolysis of benzyl ethers of myoinositol is selective and its rate varies with the nature and configuration of the neighbouring groups. The penta-acetate of 1-O-benzylmyoinositol is readily obtained from 1,4,5,6-tetra-O-benzylmyoinositol; hydrogenolysis gives 1,2,4,5,6-penta-O-acetylmyoinositol.

  肌醇苄醚的乙酰水解是选择性的，其速率随相邻基团的性质和构型而变化。1- O-苄基肌醇的五乙酸酯可容易地从1,4,5,6-四-O-苄基肌醇得到；氢解得到1,2,4,5,6-戊-O-乙酰肌醇。
• Inositol biotransformation
  申请人：University Court of the University of St Andrews

  公开号：US10131928B2

  公开（公告）日：2018-11-20

  Disclosed is a method of preparing pure or substantially pure D-myo-inositol-3-phosphate from glucose-6-phosphate and/or fructose-6-phosphate. The method may also be applied to protected and/or derivative forms of glucose-6-phosphate and/or fructose-6-phosphate so as to form protected/derivative forms of D-myo-inositol-3-phosphate, for use in further chemical reactions. The enzyme D-myo-inositol-3-phosphate synthase (INO1) is contacted with the glucose-6-phosphate and/or fructose-6-phosphate to generate labeled or unlabeled, protected or unprotected D-myo-inositol-3-phosphate, which may be further reacted and/or purified.

  本发明公开了一种从葡萄糖-6-磷酸和/或果糖-6-磷酸制备纯的或基本纯的 D-肌醇-3-磷酸的方法。该方法还可用于葡萄糖-6-磷酸和/或果糖-6-磷酸的保护形式和/或衍生物形式，从而形成 D-肌醇-3-磷酸的保护形式/衍生物形式，用于进一步的化学反应。D-肌醇-3-磷酸合成酶（INO1）与葡萄糖-6-磷酸和/或果糖-6-磷酸接触，生成标记或未标记、受保护或未受保护的 D-肌醇-3-磷酸，可进一步反应和/或纯化。