6-O-allyl-3,4,5-tri-O-benzyl-L-myo-inositol | 131233-71-1

• 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: 6-O-allyl-3,4,5-tri-O-benzyl-L-myo-inositol
• 英文别名: (1S,2R,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-prop-2-enoxycyclohexane-1,2-diol
• CAS: 131233-71-1
• 化学式: C₃₀H₃₄O₆
• 分子量: 490.596
• InChiKey: FCFCHTVNSSOGKC-CGJNDEMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-O-allyl-3,4,5-tri-O-benzyl-L-myo-inositol 在 potassium tert-butylate 、 四丁基溴化铵 、 sodium hydride 、 二正丁基氧化锡 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成
  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
• 作为产物：
  描述：

  (+/-)-3,4-di-O-benzyl-1,2:5,6-di-O-isopropylidene-myo-inositol 在 吡啶 、 盐酸 、 sodium hydroxide 、 四丁基溴化铵 、 sodium hydride 、 二正丁基氧化锡 、 对甲苯磺酸 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 13.58h， 生成 6-O-allyl-3,4,5-tri-O-benzyl-L-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

• Dimethyltin Dichloride Catalyzed Regioselective Alkylation of<i>cis</i>-1,2-Diols at Room Temperature
  作者：Varma Saikam、Saidulu Dara、Mahipal Yadav、Parvinder Pal Singh、Ram A. Vishwakarma

  DOI：10.1021/acs.joc.5b01898

  日期：2015.12.18

  mild and general method for the regioselective installation of benzyl, allyl, para-methoxybenzyl and naphthyl groups on cis-1,2-diols. The optimized method operates at room temperature using dimethyltin dichloride as catalyst and silver oxide as an additive. The present method works well with both sugars (such as mono- and disaccharides) and nonsugars (such as inositols, propan-1,2-diol, 1,2-cycloalkanediols

  在这里，我们已经开发出一种温和的通用方法，用于在顺式-1，2-二醇上区域选择性地安装苄基，烯丙基，对甲氧基苄基和萘基。该优化方法在室温下使用二氯化二甲基锡作为催化剂，氧化银作为添加剂进行操作。本方法对于糖类（例如单糖和二糖）和非糖类（例如肌醇，1，2-丙二醇，1,2-环烷二醇和脱水赤藓糖醇）均适用，并且还提供了相对更好的官能团相容性。
• Synthesis of new fluorescently labeled glycosylphosphatidylinositol (GPI) anchors
  作者：Varma Saikam、Riya Raghupathy、Mahipal Yadav、Veeranjaneyulu Gannedi、Parvinder Pal Singh、Naveed A. Qazi、Sanghapal D. Sawant、Ram A. Vishwakarma

  DOI：10.1016/j.tetlet.2011.06.005

  日期：2011.8

  The borondipyrromethene (BODIPY) labeled new glycosylphosphatidylinositol (GPI) molecules were synthesized as cellular probes to study the chemical basis of microdomain organization of GPI-anchored proteins and cholesterol in plasma membrane. The synthesis enabled by a new stereo-selective glycosylation of myo-d-inositol acceptor led to the preparation of optically pure glucosaminyl-(1-6)-α-phosph

  合成了硼联苯二甲亚甲基（BODIPY）标记的新糖基磷脂酰肌醇（GPI）分子作为细胞探针，研究了GPI锚定蛋白质和质膜中胆固醇的微区组织的化学基础。合成能够通过一个新的立体选择性糖基化肌醇- d肌醇受体导致光学纯glucosaminyl-（1-6）-α-磷脂酰的制备肌醇- d肌醇和其非天然立体异构体。
• 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：——
• Substituted inositols and their use
  申请人：Rademacher William Thomas

  公开号：US20050143290A1

  公开（公告）日：2005-06-30

  Inositol phosphate esters and conjugates formed between the compounds and a coupling partner are disclosed, in particular compounds based on a myo-inositol which is substituted at position 1 with a phosphate ester group, at position 2 with a sugar group and at position 4 and/or position 6 with an amino acid group. The compounds are based on the structure of phosphatidylinositol hexamannosides (PIM6) of Mycobacteria and may be used as mimics of the naturally occurring PIMs in order to induce biological responses normally attributed to the natural compound or may be used as biologically inert carriers in order to deliver specific pharmaceutically active compounds to lipid rafts/caveolae.