2,6-di-O-benzyloxymethyl-3,4,5-tri-O-p-methoxybenzyl-D-myo-inositol | 137897-32-6

• 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: 2,6-di-O-benzyloxymethyl-3,4,5-tri-O-p-methoxybenzyl-D-myo-inositol
• 英文别名: D-2,6-di-O-benzyloxymethyl-3,4,5-tri-O-methoxybenzyl-myo-inositol
• CAS: 137897-32-6
• 化学式: C₄₆H₅₂O₁₁
• 分子量: 780.912
• InChiKey: HUXMGFMXQYJHNE-NXINJGQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.26
• 重原子数：
  57.0
• 可旋转键数：
  22.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  112.53
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  2,6-di-O-benzyloxymethyl-3,4,5-tri-O-p-methoxybenzyl-D-myo-inositol 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.0h， 以94.1%的产率得到D-2,6-di-O-benzyloxymethyl-myo-inositol
  参考文献：
  名称：

  对映体纯天然肌醇及其非对映异构体的新型合成。

  摘要：

  已经发现各种肌醇多磷酸盐引发许多重要的生物学过程。尽管在过去的十年中已经发现了这种磷酸肌醇信号系统的知识，但许多因素仍不清楚。由于这个原因，对D-肌醇特别是新颖类似物的供应的需求增加，以更详细地研究这些生物学机制。在此，我们报告了从6-O-乙酰基-5-烯吡喃糖苷开始的肌醇所有非对映异构体的高效合成。发现用催化量的二氯化钯可以有效地进行6-O-乙酰基-5-烯吡喃糖苷到相应的取代的环己酮的转化（费里尔-II重排）。所获得的β-羟基酮的立体选择性还原提供了所有肌醇非对映异构体的前体，具有良好至优异的产率以及高的立体选择性。这些对映体纯的肌醇非对映异构体的良好可及性导致D-肌醇1,4,5-三磷酸和D-肌醇1,3,4,5-四磷酸的有效合成。

  DOI：

  10.1021/jo001575h
• 作为产物：
  描述：

  methyl 4,6-di-O-methoxybenzylidene-2,3-di-O-methoxybenzyl-α-D-glucopyranoside 在 palladium dichloride 吡啶 、 4-二甲氨基吡啶 、 sodium hydroxide 、 三甲基氯硅烷 、 3 A molecular sieve 、 sodium cyanoborohydride 、 三乙胺 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 、 tetramethylammonium triacetoxyborohydride 作用下， 以 1,4-二氧六环 、 甲醇 、 水 、 溶剂黄146 、 二甲基亚砜 、 1,2-二氯乙烷 、 乙腈 、 苯 为溶剂， 反应 38.5h， 生成 2,6-di-O-benzyloxymethyl-3,4,5-tri-O-p-methoxybenzyl-D-myo-inositol
  参考文献：
  名称：

  对映体纯天然肌醇及其非对映异构体的新型合成。

  摘要：

  已经发现各种肌醇多磷酸盐引发许多重要的生物学过程。尽管在过去的十年中已经发现了这种磷酸肌醇信号系统的知识，但许多因素仍不清楚。由于这个原因，对D-肌醇特别是新颖类似物的供应的需求增加，以更详细地研究这些生物学机制。在此，我们报告了从6-O-乙酰基-5-烯吡喃糖苷开始的肌醇所有非对映异构体的高效合成。发现用催化量的二氯化钯可以有效地进行6-O-乙酰基-5-烯吡喃糖苷到相应的取代的环己酮的转化（费里尔-II重排）。所获得的β-羟基酮的立体选择性还原提供了所有肌醇非对映异构体的前体，具有良好至优异的产率以及高的立体选择性。这些对映体纯的肌醇非对映异构体的良好可及性导致D-肌醇1,4,5-三磷酸和D-肌醇1,3,4,5-四磷酸的有效合成。

  DOI：

  10.1021/jo001575h

文献信息

• Efficient Asymmetric Synthesis of Phosphatidyl-D-myo-inositol 3,4,5-trisphosphate.
  作者：Takayuki SAWADA、Ryuichi SHIRAI、Shigeo IWASAKI

  DOI：10.1248/cpb.45.1521

  日期：——

  Phosphatidyl-D-myo-inositol 3, 4, 5-trisphosphate, a candidate of the second messenger in cellular signal transduction, was efficiently synthesized in a homochiral form.

  细胞信号转导中的第二信使候选物质磷脂酰-D-肌醇-3,4,5-三磷酸以同手性形式被高效合成。
• Synthesis of diacylglycerol analogs of phosphatidylinositol 3,4,5-trisphosphate
  作者：Ryuichi Shirai、Koji Morita、Asuka Nishikawa、Noriyuki Nakatsu、Yasuhisa Fukui、Naoko Morisaki、Yuichi Hashimoto

  DOI：10.1016/s0040-4039(98)02151-0

  日期：1998.12

  Phosphatidylinositol 3,4,5-trisphosphate analogs with saturated diacylglycerol substructure have been designed, focusing on their feactivity with PIP3 5-phosphatase. Dephosphorylation of native PIP3 was competitively inhibited in the presence of synthetic PIP3C2 and PIP3C4, respectively.

  已经设计了具有饱和二酰基甘油亚结构的磷脂酰肌醇3,4,5-三磷酸类似物，着眼于它们与PIP3 5-磷酸酶的活性。在合成PIP3 C2和PIP3 C4的存在下，天然PIP3的去磷酸化受到竞争性抑制。
• Phosphorylation of Unnatural Phosphatidylinositols with Phosphatidylinositol 3-Kinase
  作者：Naoko Morisaki、Koji Morita、Asuka Nishikawa、Noriyuki Nakatsu、Yasuhisa Fukui、Yuichi Hashimoto、Ryuichi Shirai

  DOI：10.1016/s0040-4020(00)00161-7

  日期：2000.4

  Phosphatidylinositol analogs (PIC2PIC18) having a series of saturated fatty acid (C2-C18) at sn-2 position were synthesized and subjected to the phosphorylation reaction with phosphatidylinositol 3-kinase (PI 3-kinase). The reactivity of PIC8 with PI 3-kinase turned out to be comparable to that of natural PI, although PIC18 was not phosphorylated under the same condition. The chirality of sn-2 center was not responsible for the phosphorylation reaction. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Synthesis of Phosphotriester Analogues of the Phosphoinositides PtdIns(4,5)P₂ and PtdIns(3,4,5)P₃
  作者：Qu-Ming Gu、Glenn D. Prestwich

  DOI：10.1021/jo961226g

  日期：1996.1.1

  A synthetic route was developed for the preparation of novel O-(3-aminopropyl) tethered phosphotriester analogs (5) of phosphatidylinositol 4,5-bisphosphate (PtdIns(4,5,)P-2, or PIP2) and phosphatidylinositol 3,4,5-trisphosphate (PtdIns(3,4,5)P-3, or PIP3) using the coupling reagent 2-cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite. The phosphotriester ligand design introduced a reactive aminopropyl group at the polar lipid head of the ring-phosphorylated phosphoinositides, allowing a reporter moiety to be positioned at the surface of the bilayer and in the vicinity of the phosphorylated inositol. Such reporter groups may interact with membrane-proximal regions of PIP2- and PIP3-binding proteins recruited to membrane sites by electrostatic interactions between the phosphates of the phospholipid and basic regions of the proteins. Following a convergent strategy, phosphitylation of an optically-pure 1,2-O-diacyl-sn-glycerol with 2-cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite was followed by coupling with protected inositol precursors to give adducts 8 in 80% to 95% yield. The 2-cyanoethyl phosphotriester was stable during the subsequent reaction steps and could be conveniently converted to the 3-aminopropyl group during the final hydrogenolysis of the benzyl protecting groups. Benzophenone-containing photoaffinity probes of the phosphotriester IIa and IIb were also synthesized. Alternatively, the versatile cyanoethyl group could be removed using diisopropylethylamine prior to hydrogenolysis, thereby furnishing the corresponding phosphodiesters, PIP3 and PIP2 (13a and 13b).
• Synthesis of Photoactivatable 1,2-<i>O-</i>Diacyl-<i>sn-</i>glycerol Derivatives of 1-<scp>l</scp>-Phosphatidyl-<scp>d</scp>-<i>myo</i>-inositol 4,5-Bisphosphate (PtdInsP₂) and 3,4,5-Trisphosphate (PtdInsP₃)
  作者：Jian Chen、Adam A. Profit、Glenn D. Prestwich

  DOI：10.1021/jo960895r

  日期：1996.1.1

  Photoactivatable analogues of 1-L-phosphatidyl-D-myo-inositol 4,5-bisphosphate (PtdIns(4,5)P-2 or PtdInsP(2)) and the corresponding 3,4,5-trisphosphate (PtdIns(3,4,5)P-3 or PtdInsP(3)) were prepared from the two chiral precursors, methyl a-D-glucopyranoside and 1,2-isopropylidene-sn-glycerol. Two key synthetic transformations included the Ferrier rearrangement reaction to construct the optically-pure inositol skeleton and the sequential acylation of the primary and secondary hydroxyl groups on the glycerol derivatives. The sn-1-O-(6-aminohexanoyl) PtdInsP(2) and PtdInsP(3) derivatives were further modified to contain benzophenone photophores in unlabeled and high specific activity tritium-labeled forms.