(2R,3R,4R)-1,3,4-tris(phenylmethoxy)hept-6-en-2-ol | 157736-63-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2R,3R,4R)-1,3,4-tris(phenylmethoxy)hept-6-en-2-ol
• CAS: 157736-63-5
• 化学式: C₂₈H₃₂O₄
• 分子量: 432.56
• InChiKey: DMUVLRAPODKPBE-JCYYIGJDSA-N

物化性质

• 沸点：
  572.3±50.0 °C(Predicted)
• 密度：
  1.113±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  32
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R)-1,3,4-tris(phenylmethoxy)hept-6-en-2-ol 在 Grubbs catalyst first generation palladium diacetate 、 1,10-菲罗啉 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 生成 1,6-anhydro-4,5,7-tri-O-benzyl-2,3-dideoxy-D-glucosept-1-enitol
  参考文献：
  名称：

  以碳水化合物为基础的氧杂环丁烷：环戊二糖，用于合成琼脂糖

  摘要：

  描述了一种基于碳水化合物的奥氮平家族的闭环复分解（RCM）方法。各种容易获得的，受保护的单糖衍生的二烯被用来证明合成序列的实用性，并研究使用Grubbs或Schrock催化剂如何诸如刚性化和脱氧性等因素介导RCM。七元环状烯醇醚是用于合成琼脂糖碳水化合物的扩环糖基。

  DOI：

  10.1016/s0040-4039(03)00849-9
• 作为产物：
  描述：

  3,4,6-三苄氧基-D-葡萄烯糖 在 N-碘代丁二酰亚胺 、 正丁基锂 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 21.25h， 生成 (2R,3R,4R)-1,3,4-tris(phenylmethoxy)hept-6-en-2-ol
  参考文献：
  名称：

  Ring-opening reactions of iminosugar-derived aziridines: application to the general synthesis of α-1-C-substituted derivatives of fagomine

  摘要：

  A general approach to alpha-l-C-substituted derivatives of fagomine (2-deoxynojirimycin-alpha-C-glycosides) by ring-opening reactions of an aziridine with various heteroatomic nucleophiles, including thiol, amine, alcohol, carboxylate and phosphate, is reported. The nine-step reaction sequence proceeded in an overall yield of 14-28% from tri-O-benzyl-D-glucal. In the course of this study, the synthesis of alpha-1-C-ethyl-fagomine as well as of 1,N-anhydro derivatives of fagomine has been achieved for the first time. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00364-1

文献信息

• Intramolecular metal-catalyzed amination of pseudo-anomeric C–H bonds
  作者：Sylvestre Toumieux、Philippe Compain、Olivier R. Martin

  DOI：10.1016/j.tetlet.2005.05.043

  日期：2005.7

  MgO provided original spirooxazolidines or spirooxathiazolidines in reasonable yields. No correlation between ‘anomeric’ stereochemistry and insertion efficiency was found for the conversion of carbamate derivatives whereas amination reactions of the corresponding sulfamate esters were found to be strongly dependent on the anomeric configuration.

  据报道分子内金属催化了C-糖苷中假异头CH键的胺化反应。α，β-的治疗ç -carbamoyloxymethyl-或β- Ç -sulfamoyloxymethyl苷用的Rh 2（OAc）4，岛（OAC）2和MgO在合理的产率提供原始spirooxazolidines或spirooxathiazolidines。对于氨基甲酸酯衍生物的转化，未发现“异头”立体化学与插入效率之间的相关性，而发现相应的氨基磺酸酯的胺化反应强烈依赖于异头构型。
• Chemistry of Imino Glycals: Preparation and Application to the Synthesis of (+)-Fagomine
  作者：Jérôme Désiré、Paul J. Dransfield、Paul M. Gore、Michael Shipman

  DOI：10.1055/s-2001-16039

  日期：——

  The synthesis of imino glucal 2 from tri-O-benzyl-d-glucal in 8 steps is described. This novel imino sugar building block is further converted into (+)-fagomine by a two-step hydrogenation sequence.

  本文介绍了通过 8 个步骤从三-O-苄基-d-葡萄糖醛合成亚氨基葡萄糖醛 2 的过程。这种新颖的亚氨基糖结构单元通过两步氢化程序进一步转化为 (+)- 法戈明。
• Stereochemical control in the oxymercuration of 5-alken-1-ols
  作者：Marcus A. Tius、Jakob Busch-Petersen

  DOI：10.1016/s0040-4039(00)77058-4

  日期：1994.7

  The axial preference which had been observed during the intramolecular reaction of cannabinoid precursors 2 and 3 is not a heteroatom-mediated directing effect. Rather, it reflects a kinetic preference which may be related to the anomeric effect.

  在大麻素前体2和3的分子内反应过程中观察到的轴向优先性不是杂原子介导的导向作用。相反，它反映出可能与异头作用有关的动力学偏好。
• Carbohydrate-based oxepines: ring expanded glycals for the synthesis of septanose saccharides
  作者：Mark W. Peczuh、Nicole L. Snyder

  DOI：10.1016/s0040-4039(03)00849-9

  日期：2003.5

  investigate how factors such as rigidification and deoxygenation mediate RCM using the Grubbs or Schrock catalyst. The seven-membered cyclic enol ethers are ring expanded glycals to be used in the synthesis of septanose carbohydrates.

  描述了一种基于碳水化合物的奥氮平家族的闭环复分解（RCM）方法。各种容易获得的，受保护的单糖衍生的二烯被用来证明合成序列的实用性，并研究使用Grubbs或Schrock催化剂如何诸如刚性化和脱氧性等因素介导RCM。七元环状烯醇醚是用于合成琼脂糖碳水化合物的扩环糖基。
• Ring-opening reactions of iminosugar-derived aziridines: application to the general synthesis of α-1-C-substituted derivatives of fagomine
  作者：Jean-Yves Goujon、David Gueyrard、Philippe Compain、Olivier R. Martin、Naoki Asano

  DOI：10.1016/s0957-4166(03)00364-1

  日期：2003.7

  A general approach to alpha-l-C-substituted derivatives of fagomine (2-deoxynojirimycin-alpha-C-glycosides) by ring-opening reactions of an aziridine with various heteroatomic nucleophiles, including thiol, amine, alcohol, carboxylate and phosphate, is reported. The nine-step reaction sequence proceeded in an overall yield of 14-28% from tri-O-benzyl-D-glucal. In the course of this study, the synthesis of alpha-1-C-ethyl-fagomine as well as of 1,N-anhydro derivatives of fagomine has been achieved for the first time. (C) 2003 Elsevier Ltd. All rights reserved.