4-O-(4-methoxytetrahydropyran-4-yl)-2,3:5,6-di-O-isopropylidene-D-myo-inositol | 119874-38-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-O-(4-methoxytetrahydropyran-4-yl)-2,3:5,6-di-O-isopropylidene-D-myo-inositol
• CAS: 119874-38-3
• 化学式: C₁₈H₃₀O₈
• 分子量: 374.431
• InChiKey: ACUZPKNZJAUUQX-SOAFEQHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.94
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  84.84
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  4-O-(4-methoxytetrahydropyran-4-yl)-2,3:5,6-di-O-isopropylidene-D-myo-inositol 在 platinum(IV) oxide 吡啶 、 MSNT 、 Amberlite IRC-50 、 水 、 氢气 作用下， 以 乙醇 为溶剂， 生成 磷脂酰肌醇
  参考文献：
  名称：

  1,2-二棕榈酰基-甘油-3-基---肌醇1-磷酸酯的合成。

  摘要：

  提出了合成纯的1,2-二棕榈酰-sn-甘油-3-基-肌醇1-磷酸酯的简便方法。

  DOI：

  10.1016/s0040-4039(00)82254-6
• 作为产物：
  描述：

  1-O-(tert-butyldiphenylsilyl)-4-O-camphanyl-2,3:5,6-di-O-isopropylidene-D-myo-inositol 在 氢氧化钾 、 四丁基氟化铵 、 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 生成 4-O-(4-methoxytetrahydropyran-4-yl)-2,3:5,6-di-O-isopropylidene-D-myo-inositol
  参考文献：
  名称：

  1,2-二棕榈酰基-甘油-3-基---肌醇1-磷酸酯的合成。

  摘要：

  提出了合成纯的1,2-二棕榈酰-sn-甘油-3-基-肌醇1-磷酸酯的简便方法。

  DOI：

  10.1016/s0040-4039(00)82254-6

文献信息

• Total synthesis of the four stereoisomers of dihexadecanoyl phosphatidylinositol and the substrate stereospecificity of human erythrocyte membrane phosphatidylinositol 4-kinase
  作者：Rodney C. Young、C. Peter Downes、Drake S. Eggleston、Martin Jones、Colin H. Macphee、Kishore K. Rana、John G. Ward

  DOI：10.1021/jm00164a027

  日期：1990.2

  substrates for a partially purified phosphatidylinositol 4-kinase (EC 2.7.1.67) derived from human erythrocyte membranes revealed that the chirality of the inositol ring is crucial for efficient phosphorylation, whereas the chirality of the glycerol moiety is relatively unimportant. Moreover, the similarity in phosphorylation rates of the naturally occurring mammalian phospholipid, I, and its synthetic stereochemical

  已经开发了一种新的方便的方法来制备二十六烷酰基磷脂酰肌醇的四种立体异构体。以高收率合成对映体对酸不稳定，受五保护的肌醇构件，并将其与手性苯基二十六烷酰基甘油基磷酸酯偶联，得到完全保护的磷脂酰肌醇。随后通过在乙醇水溶液中的氢解和自水解作用将它们脱保护，得到所需的纯产物。比较这些化合物作为衍生自人红细胞膜的部分纯化的磷脂酰肌醇4-激酶（EC 2.7.1.67）的潜在底物的过程表明，肌醇环的手性对于有效的磷酸化至关重要，而甘油部分的手性相对不重要。此外，
• Inhibition of human erythrocyte membrane phosphatidylinositol 4-kinase by phospholipid analogues
  作者：RC Young、CP Downes、M Jones、KJ Milliner、KK Rana、JG Ward

  DOI：10.1016/0223-5234(94)90146-5

  日期：1994.1

  Analogues of phosphatidylinositol (Ptdlns, 1) have been synthesized to investigate the structural requirements for inhibition of a Ptdlns 4-kinase obtained from human erythrocyte membranes. While the presence of either D-1 or D-3 Stereochemistry in the inositol moiety greatly influences the degree of inhibition produced by Ptdlns analogues, the stereochemistry of the glycerol moiety is of little consequence. Neither structural feature, however, makes a significant contribution to binding affinity. Competitive inhibitory activity was found to be retained (or even enhanced) in substantially simpler analogues consisting of 1 or 2 hydrocarbon chains attached to a charged phosphate head group, such as in the phosphatidic acids, 24 and 26. The observation that the phosphatidylinositol 4-phosphate (Ptdlns 4P) and phosphatidic acid analogues (eg, 16 or 17, and 26 respectively) inhibit Ptdlns 4-kinase may suggest that such species have a regulatory role in Ptdlns turnover.
• General Method for the Synthesis of Phospholipid Derivatives of 1,2-O-Diacyl-sn-Glycerols
  作者：Stephen F. Martin、John A. Josey、Yue-Ling Wong、Daniel W. Dean

  DOI：10.1021/jo00096a023

  日期：1994.8

  An efficient phosphite coupling protocol is described for the syntheses of the major classes of phospholipids that are derived from 1,2-O-diacyl-sn-glycerols and analogues thereof. The symmetrical diacyl glycerols 10c,d were prepared by straightforward acylation of 3-O-benzyl-sn-glycerol (7) with the appropriate carboxylic acid in the presence of dicyclohexylcarbodiimide (DCC) and 4-(dimethylamino)pyridine (DMAP). A simple method for preparing saturated and unstaturated mixed 1,2-O-diacyl-sn-glycerols was then devised that involved stepwise acylation of 7 with different alkyl carboxylic acids and debenzylation this procedure is exemplified by the preparation of 10a,b. The 1,2-O-diacyl-sn-glycerols 10a-d were then coupled with suitably protected lipid head groups employing reactive alkyl or aryl dichlorophosphites to give intermediate phosphite triesters in high overall yields. Oxidation or sulfurization of these phosphites proceeded smoothly to give the corresponding phosphate or phosphorothioate triesters, deprotection of which then provided the phosphatidylcholines 16 and 17, the phosphatidylethanolamine 20, the phosphatidylserine 28, and the phosphatidylinositols 37 and 38. Preparation of 37 and 38 required the invention of an improved method for resolving the isopropylidene-protected D-myo-inositol derivative 33. This phosphite coupling procedure was modified to assemble phospholipids bearing-polyunsaturated acyl side chains at the sn-2-position as exemplified by the preparation of the phosphatidylethanolamine 26. The one-pot phosphite coupling procedure is also applicable to the syntheses of a variety of other biologically interesting phospholipid analogues. For example, the phosphatidylinositol analogues 49-51, in which the hydroxyl group at C(2) of the inositol ring has been modified, were prepared in excellent overall yields by conjoining the 1,2-O-diacyl-sn-glycerol 10c with the protected inositol derivatives 44, 45, and 48. Phospholipid analogues that contain other replacements of the phosphate group including phosphoramidates and thiophosphates maybe prepared as evidenced by the syntheses of 56 and 61 in which the sn-3 oxygen atom of the 1,2-O-diacyl-sn-glycerol moiety is replaced with an N-benzyl group or a sulfur atom, respectively.
• WARD, JOHN G.;YOUNG, RODNEY C., TETRAHEDRON LETT., 29,(1988) N 46, C. 6013-6016
  作者：WARD, JOHN G.、YOUNG, RODNEY C.

  DOI：——

  日期：——