2,3:5,6-二-O-亚环己基1-O-(苯基甲基)-D-肌醇 | 23393-20-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2,3:5,6-二-O-亚环己基1-O-(苯基甲基)-D-肌醇
• 英文名称: 2,3:5,6-Di-O-cyclohexylidene-1-O-(phenylmethyl)-D-myo-inositol
• 英文别名: (+/-)-3-O-benzyl-1,2:4,5-di-O,O-cyclohexylidene-myo-inositol；3-O-benzyl-1,2:4,5-di-O-cyclohexylidene-D-myo-inositol；3-O-benzyl-1,2:4,5-di-O-cyclohexylidene-L-myo-inositol；D-1-O-benzyl-2,3:5,6-di-O-cyclohexylidene-myo-inositol；(-)-3-benzyl-1,2:4,5-dicyclohexylidene-D-myo-inositol；(-)-3-benzyl-1,2:4,5-dicyclohexylidene-myo-inositol
• CAS: 23393-20-6；111901-82-7；126722-28-9；134109-10-7；134109-11-8；136375-66-1；120202-94-0
• 化学式: C₂₅H₃₄O₆
• 分子量: 430.541
• InChiKey: PPOJVXPBBLVDSK-JIKXHTODSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.84
• 重原子数：
  31.0
• 可旋转键数：
  3.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  66.38
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2,3:5,6-二-O-亚环己基1-O-(苯基甲基)-D-肌醇 在 溶剂黄146 作用下， 反应 1.0h， 生成 1L-1-O-benzyl-myo-inositol
  参考文献：
  名称：

  Synthesis of mycothiol, 1D-1-O-(2-[N-acetyl-l-cysteinyl]amino-2-deoxy-α-d-glucopyranosyl)-myo-inositol, principal low molecular mass thiol in the actinomycetes

  摘要：

  Members of the actinomycetes produce 1D-1-O-(2-[N-acetyl-L-cysteinyl]amino-2-deoxy-alpha-D-glucopyranosyl)-myo-inositol or mycothiol 1 as principal low molecular mass thiol, Chemical synthesis of a biosynthetic precursor of mycothiol, the pseudodisaccharide 1D-1-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-myo-inositol 13 was achieved by the following steps: (1) Enantioselcctive synthesis gave the glycosyl acceptors (-)-2,3,4,5,6-penta-O-acetyl-D-myo-inositol D-7 and the corresponding L-isomer L-7. (2) Condensation of D-7 and L-7 with the glycosyl donor 3,4,6-tri-O-acetyl-2-deoxy-2-(2,4-dinitrophenylamino)-alpha-D-glucopyranosylbromide afforded the corresponding alpha and beta anomeric products, which could be resolved by silica gel chromatography, (3) Deprotection of these by hydrolysis using an anion exchange resin gave 1D- and 1L-1-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-myo-inositol 13 and 15 and the corresponding beta-coupled anomers 14 and 16. Only 13, and to a much lesser extent 15, were used by enzymes present in an ammonium sulphate fraction of a cellfree extract of Mycobacterium smegmatis for the enzymatic synthesis of mycothiol. In the absence of acetyl-SCoA, the immediate biosynthetic precursor of 1, desacetylmycothiol, was the major product. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00383-2
• 作为产物：
  描述：

  Inositol 在 4-二甲氨基吡啶 、 氢氧化钾 、 sodium hydride 、 对甲苯磺酸 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 47.0h， 生成 2,3:5,6-二-O-亚环己基1-O-(苯基甲基)-D-肌醇
  参考文献：
  名称：

  First Total Synthesis of Mycothiol and Mycothiol Disulfide

  摘要：

  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.

  DOI：

  10.1021/ol0362008

文献信息

• The total synthesis of myo-inositol polyphosphates
  作者：Joseph P. Vacca、S.Jane deSolms、Joel R. Huff、David C. Billington、Raymond Baker、Janusz J. Kulagowski、Ian M. Mawer

  DOI：10.1016/s0040-4020(01)89510-7

  日期：1989.1

  Total synthesis of the individual enantiomers of myo-inositol 4-phosphate (), myo-inositol 1,4-bisphosphate () and myo-inositol 1,4,5-trisphosphate (), together with syntheses of racemic myo-inositol 1,3,4-trisphosphate () and myo-inositol 2,4,5-trisphosphate () are reported. The syntheses feature the use of camphanic acid esters for resolution of protected inositols, and the use of tetrabenzylpyrophosphate

  分别合成肌醇4-磷酸酯（），肌醇1,4-二磷酸（）和肌醇1,4,5-三磷酸（）的各个对映异构体，以及外消旋肌醇1的合成，据报道有3,4-三磷酸（）和肌醇2,4,5-三磷酸（）。合成的特征在于使用樟脑酸酯来拆分受保护的肌醇，以及使用焦磷酸四苄基酯作为多羟基醇的有效磷酸化剂。
• 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 phosphatidylinositol mannosides (PIMs)
  作者：Andreas Stadelmaier、Richard R Schmidt

  DOI：10.1016/j.carres.2003.06.002

  日期：2003.11

  Two strategies towards the synthesis of phosphatidylinositol mannosides (PIMs) were elaborated which permit selective access to the O-1-, O-2-, and the O-6 position of the myo-inositol residue. Starting materials are 1,2:5,6- and 1,2:4,5-di-O-cyclohexylidene-DL-myo-inositol, respectively. In the latter case, the required assignment to the D- or L-series is based on the transformation of one enantiomer

  详细说明了两种合成磷脂酰肌醇甘露糖苷（PIM）的策略，它们可以选择性地进入肌醇残基的O-1-，O-2-和O-6位置。起始原料分别是1,2：5,6-和1,2：4,5-二-O-环己叉基-DL-肌醇。在后一种情况下，对D系列或L系列的要求分配是基于一种对映异构体向已知（-）-liriodentritol的转化。两种方法的效率和潜在的多功能性在合成都具有肉豆蔻酰基残基作为磷脂酰部分的PIMs（D）-1a及其假对映体（L）-1b中得到了例证。
• Cottaz, Sylvain; Brimacombe, John S.; Ferguson, Michael A. J., Journal of the Chemical Society. Perkin transactions I, 1993, # 23, p. 2945 - 2952
  作者：Cottaz, Sylvain、Brimacombe, John S.、Ferguson, Michael A. J.

  DOI：——

  日期：——
• Phospholipids chiral at phosphorus. 18. Stereochemistry of phosphatidylinositide-specific phospholipase C
  作者：Gialih Lin、Ming Daw Tsai

  DOI：10.1021/ja00190a074

  日期：1989.4