1(3),2,4(6),5,6(4)-penta-O-acetyl-sn-myoinositol | 35519-39-2

• 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: 1(3),2,4(6),5,6(4)-penta-O-acetyl-sn-myoinositol
• 英文别名: (+)-2,3,4,5,6-penta-O-acetyl-L-myo-inositol；2,3,4,5,6-penta-O-acetyl-sn-myo-inositol；2,3,4,5,6-penta-O-acetyl-sn-myoinositol；D-2,3,4,5,6-penta-O-acetyl-myo-inositol；1D-2,3,4,5,6-Penta-O-acetyl-myo-inositol
• CAS: 35519-39-2
• 化学式: C₁₆H₂₂O₁₁
• 分子量: 390.344
• InChiKey: STEDFOFWVUHEQP-CMXYNOPPSA-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：

  1(3),2,4(6),5,6(4)-penta-O-acetyl-sn-myoinositol 在 platinum(IV) oxide 吡啶 、 氢气 作用下， 生成 Acetic acid (1R,2S,3S,4R,5R,6S)-2,3,4,5-tetraacetoxy-6-phosphonooxy-cyclohexyl ester
  参考文献：
  名称：

  Lyutik,A.I. et al., Journal of general chemistry of the USSR, 1974, vol. 44, p. 2559

  摘要：

  DOI：
• 作为产物：
  描述：

  1(3),4(6),5,6(4)-tetra-O-acetyl-sn-myoinositol 在 吡啶 、 盐酸 、 溶剂黄146 作用下， 以 氯仿 为溶剂， 反应 5.83h， 生成 1(3),2,4(6),5,6(4)-penta-O-acetyl-sn-myoinositol
  参考文献：
  名称：

  Stepanov, A. E.; Sibrikov, Yu. I.; Shvets, V. I., Journal of Organic Chemistry USSR (English Translation), 1980, vol. 16, p. 1946 - 1950

  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。
• Nickel-catalyzed α-glycosylation of C(1)-hydroxyl<scp>d</scp>-myo-inositol: a formal synthesis of mycothiol
  作者：Matthew S. McConnell、Fei Yu、Hien M. Nguyen

  DOI：10.1039/c2cc35823a

  日期：——

  Formal synthesis of mycothiol has been developed via nickel-catalyzed α-glycosylation of the C(1)-hydroxyl group of D-myo-inositols with C(2)-N-substituted benzylideneamino N-phenyl trifluoroacetimidate donors. The pseudo-oligosaccharides were obtained in good yield and with excellent α-selectivity. Removal of the C(2)-N-2-trifluoromethylphenyl-benzylidene group under mild conditions provides a pseudo-disaccharide, completing the formal synthesis of mycothiol.

  mycothiol 的正式合成是通过镍催化 D-myo-肌醇的 C(1)-羟基与 C(2)-N-取代的亚苄基氨基 N-苯基三氟乙酰亚胺酯供体的 α-糖基化来开发的。所获得的假低聚糖具有良好的产率和优异的α选择性。在温和条件下去除C(2)-N-2-三氟甲基苯基-亚苄基基团提供假二糖，完成菌硫醇的正式合成。
• 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。
• First Total Synthesis of Mycothiol and Mycothiol Disulfide
  作者：Sungwon Lee、John P. N. Rosazza

  DOI：10.1021/ol0362008

  日期：2004.2.1

  The first total synthesis of mycothiol and mycothiol disulfide was achieved by linking D-2,3,4,5,6-penta-O-acetyl-myo-inositol, O-(3,4,6-tri-O-acetyl)-2-azido-2-deoxy-alpha,beta-D-glucopyranosyl) trichloroacetimidate, and N,S-diacetyl-L-cysteine and deprotecting peracetylated mycothiol. The first full spectral characterization is reported for underivatized mycothiol. The structure of mycothiol was confirmed by spectral analysis of the known bimane derivative.