(+/-) 1-O-benzyl-myo-inositol | 23486-90-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+/-) 1-O-benzyl-myo-inositol
• 英文别名: 1(3)-O-benzyl-myo-inositol；1-O-benzyl-DL-myo-inositol；1-O-Benzyl-myo-inositol；(+/-)-O-Benzyl-myo-inosit；rac.-1-O-Benzyl-myoinosit；1D-1-O-benzyl-myo-inositol；1-O-benzyl-D-myo-inositol；1-O-benzyl-L-myo-inositol；1-O-Benzyl-sn-myoinositol；1-O-Benzyl-myo-inosit
• CAS: 23486-90-0；68738-29-4
• 化学式: C₁₃H₁₈O₆
• 分子量: 270.282
• InChiKey: RWDNROPIZFGEAU-OJEZURLMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.61
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  110.38
• 氢给体数：
  5.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 (+/-) 1-O-benzyl-myo-inositol 生成 (+/-)-1-O-Benzyl-myo-inosit-2,3,4,5,6-pentakis-dimethylphosphat
  参考文献：
  名称：

  Angyal,S.J.; Russell,A.F., Australian Journal of Chemistry, 1969, vol. 22, p. 391 - 404

  摘要：

  DOI：
• 作为产物：
  描述：

  溴甲苯 在 palladium on activated charcoal 四丁基溴化铵 、 二正丁基氧化锡 、 对甲苯磺酸 作用下， 以 乙醇 、 水 为溶剂， 反应 36.0h， 生成 (+/-) 1-O-benzyl-myo-inositol
  参考文献：
  名称：

  The synthesis and resolution of (±)-1,5,6-tri-O-benzyl-myo-inositol

  摘要：

  Racemic 1,5,6-tri-O-benzyl-myo-inositol was prepared by five routes and converted into 1,5,6-tri-O-benzyl-2,3-O-isopropylidene-myo-inositol, the camphanates of which were readily separated by chromatography. The absolute configurations of the chiral derivatives were established by their conversion into the known chiral 1,4,5,6-tetra-O-benzyl-myo-inositols. 1D-1,5,6-Tri-O-benzyl-2,3-O-isopropylidene-myo-inositol was converted into 1D-1,3,5,6-tetra-O-benzyl-myo-inositol and thence into 1D-2,4-di-O-methyl-myo-inositol. 1D-1,5,6-Tri-O-benzyl-myo-inositol was converted into 1D-1,2,5,6-tetra-O-benzyl-myo-inositol, the diacetate of which is a chiral analogue of "thermosalient crystals". The potential of the above compounds for the synthesis of natural products is surveyed.

  DOI：

  10.1016/0008-6215(90)80132-m

文献信息

• Improved preparation of acetals of myo-inositol and its (±)-1-benzyl ether: conformational analysis of di-O-isopropylidene-myo-inositol derivatives
  作者：Roberto Fernandez de la Pradilla、Carlos Jaramillo、Jesus Jimenez-Barbero、Manuel Martin-Lomas、Soledad Penades、Amparo Zapata

  DOI：10.1016/0008-6215(90)84052-v

  日期：1990.10

  myo -inositol with 3–5 equiv. of 2-methoxypropene or 2,2-dimethoxypropane in methyl sulfoxide or N,N -dimethylformamide gave mixtures of the 1,2:4,5-, 1,2:5,6-, and 1,2:3,4-di- O -isopropylidene derivatives with little or none of the 1,2:3,4:5,6-triacetal 5 . With ≈ 7 equiv. of 2-methoxypropene in methyl sulfoxide-hexane, 70% of 5 was obtained. Kinetic acetonation of 1- O -benzyl- myo -inositol gave

  摘要肌醇与3-5当量的酸催化反应。将2-甲氧基丙烯或2,2-二甲氧基丙烷在甲基亚砜或N，N-二甲基甲酰胺中得到1,2,4,5-，1,2：5,6-和1,2：3,4-的混合物几乎没有或没有1,2：3,4：5,6-三缩醛5的二-O-异亚丙基衍生物。≈7当量 在甲基亚砜-己烷中得到2-甲氧基丙烯，得到5的70％。1-O-苄基-肌醇的动力学丙酮化主要产生3,4：5,6-二缩醛，而热力学条件主要产生2,3：5,6-二缩醛。1-O-苄基-2,3：4,5-二-O-异亚丙基-肌醇是次要产品，主要存在于非极性溶剂的椅子构型和极性偏斜的船形结构中。溶剂，而6-乙酸盐仅采用斜舟构象。
• Synthesis of some benzyl and methyl ethers of myo-inositol
  作者：Per J. Garegg、Bengt Lindberg、Ingemar Kvarnström、Stefan C.T. Svensson

  DOI：10.1016/s0008-6215(00)90816-4

  日期：1988.3

  Abstract The 1 d and 1 d forms of 1,2,4,5,6- and 1,2,3,4,5-penta- O -methyl- myo -inositol have been prepared from the corresponding chiral mono- O -benzyl derivatives. Convenient preparations are also described of achiral derivatives of 1-, 2-, 4-, and 5- O -benzyl- myo -inositol and of achiral 1,2,4,5,6- and 1,3,4,5,6- myo -inositol by selective benzylation through stannylidene derivatives and through

  摘要从相应的手性单-O-制备了1,2,4,5,6-和1,2,3,4,5-五-O-甲基-肌醇的1 d和1 d形式。苄基衍生物。还描述了1-，2-，4-和5-O-苄基-肌醇的非手性衍生物以及非手性1,2,4,5,6-和1,3,4,5的方便制备方法， 6-肌醇通过亚苄基衍生物的选择性苄基化和亚苄基乙缩醛的还原性裂解而形成。
• 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。
• Flexible Stereo- and Regioselective Synthesis ofmyo-Inositol Phosphates(Part 2): Via Nonsymmetrical Conduritol B Derivatives
  作者：Michael A. L. Podeschwa、Oliver Plettenburg、Hans-Josef Altenbach

  DOI：10.1002/ejoc.200400918

  日期：2005.7

  myo-inositol phosphates. Optically pure compounds can be prepared, in both forms, from p-benzoquinone by enzymatic resolution of a diacetoxyconduritol key intermediate. Monosubstituted inositol derivatives can be obtained by breaking the C2 symmetry of conduritol B derivatives. A wide variety of myo-inositol phosphates can be synthesized by combining the previously reported symmetrical approach with

  一种实用的路线的制备描述肌醇肌醇磷酸盐。可以通过对乙酰氨基乙酸二硬脂醇关键中间体的酶促拆分，从对苯醌制备两种形式的光学纯化合物。单取代的肌醇衍生物可通过破坏Conduritol B衍生物的C 2对称性而获得。各种各样的肌肌醇磷酸盐可以通过组合与这个新的非对称的方法先前报道的对称方法来合成。（©Wiley-VCH Verlag GmbH＆Co.KGaA，69451 Weinheim，Germany，2005）
• 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。