meso-2,3,4,5,6-O-pentabenzyl-scyllo-ionose | 22144-57-6

• 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: meso-2,3,4,5,6-O-pentabenzyl-scyllo-ionose
• 英文别名: 1,2,3,4,5-penta-O-benzyl-scyllo-inosose；2,3,4,5-penta-O-benzyl-scyllo-inosose；1,3,4,5,6-penta-O-benzylmyoinosose；(2R,3S,5R,6S)-2,3,4,5,6 pentakis(benzyloxy)cyclohexanone；1,3,4,5,6-Penta-O-benzyl-myo-scyllo-inosose；Penta-O-benzyl-scylloinosose
• CAS: 22144-57-6
• 化学式: C₄₁H₄₀O₆
• 分子量: 628.765
• InChiKey: HPOVDBADAVTVDU-YHTOUJAXSA-N

物化性质

• 沸点：
  731.7±60.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  47.0
• 可旋转键数：
  15.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  meso-2,3,4,5,6-O-pentabenzyl-scyllo-ionose 在 sodium azide 、 18-冠醚-6 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 生成 2,4,6-tri(phenylmethyloxy)phenol
  参考文献：
  名称：

  Corey-Link反应在α-取代羧酸酯合成中作用的扩展

  摘要：

  在碱性条件下用氯仿处理 1,2:5,6-二-O-异亚丙基-α-d-核糖-己糖-3-乌洛糖，得到正常的 3-C-三氯甲基-α-d-别呋喃糖衍生物。在改进的 Corey-Link 反应条件下，但使用不同于通常叠氮化物的亲核试剂，获得了一系列 α-取代的羧酸酯（和一种酰胺）。将溴仿类似地添加到乌洛糖中形成了α-溴甲酯。从多羟基化环己酮形成“肌醇 α-氨基酸”的两次尝试都失败了。单晶 X 射线结构测定报告用于 (3S)-1,2:5,6-di-O-isopropylidene-3-C -甲氧基羰基-3-S-苯基-3-硫代-α-d-核糖-己糖，(3S)-1,2:5,6-二-O-异亚丙基-3-S-苯基-3-C-(苯硫基）羰基-3-硫代-α-d-核糖-己糖，3-deoxy-1,2:5，

  DOI：

  10.1071/ch06137
• 作为产物：
  描述：

  3,4,5,6-tetra-O-benzyl-cis-1,2-O-cyclohexylidene myo-inositol 在 chromium(III) oxide 、 氢氧化钾 、 溶剂黄146 作用下， 以 溶剂黄146 、 苯 为溶剂， 生成 meso-2,3,4,5,6-O-pentabenzyl-scyllo-ionose
  参考文献：
  名称：

  1282.环糖醇。第二十一部分。肌醇的苄醚。肌醇的甲苯磺酰基衍生物的芳构化

  摘要：

  DOI：

  10.1039/jr9650006949

文献信息

• Diastereoselective synthesis of new O-alkylated and C-branched inositols and their corresponding fluoro analogues
  作者：Charlotte Collet、Françoise Chrétien、Yves Chapleur、Sandrine Lamandé-Langle

  DOI：10.3762/bjoc.12.39

  日期：——

  Efficient routes were developed for the diastereoselective synthesis of new O-alkylated and C-branched inositols and their corresponding fluoro analogues. The key steps of the synthesis were the easy accessibility of different types of arms in term of configuration (myo and scyllo), the linking method and length, which could modulate the biological properties. These inositol derivatives, bearing an

  为新的O-烷基化和C支化肌醇及其相应的氟类似物的非对映选择性合成开发了有效的途径。合成的关键步骤是在构型方面（myo和scyllo）易于接近不同类型的臂，连接方法和长度，这可以调节生物学特性。这些肌醇衍生物带有一个被羟基或氟原子封端的臂，可能是非对映异构中间体和生物学评估（尤其是PET成像实验）感兴趣的候选物。
• WO2008/57336
  申请人：——

  公开号：——

  公开（公告）日：——
• Offer, John L.; Voorheis, H. Paul; Metcalfe, James C., Journal of the Chemical Society. Perkin transactions I, 1992, # 8, p. 953 - 960
  作者：Offer, John L.、Voorheis, H. Paul、Metcalfe, James C.、Smith, Gerry A.

  DOI：——

  日期：——
• 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.
• Inositol tetrakisphosphate from chicken eggshell
  作者：Taku Ito、Hajime Itokawa、Takanori Miyaki、Miho Kamimura、Mariko Hamano、Masaya Nakata、Yoko Saikawa

  DOI：10.1016/j.tet.2019.130853

  日期：2020.1

  Unlike our previous study that identified D-myo-inositol 4,5-bisphosphate (Ins(4,5)P-2, 1) from ostrich eggshell, the compound myo-inositol 1,4,5,6-tetrakisphosphate (Ins(1,4,5,6)P-4, 2) was isolated as an almost racemic mixture from the internal region of chicken eggshell. Furthermore, 2, 2-[H-2]-2, and amorphous CaCO3 were prepared as tools for assessment about transformation of CaCO3 during bone formation. (C) 2019 Elsevier Ltd. All rights reserved.