2-((2S,4S,5R,6R)-6-((benzyloxy)methyl)-5-methyl-4-(((2S,3R,4S,5R)-3,4,5-trimethoxytetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)acetaldehyde | 1035662-61-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-((2S,4S,5R,6R)-6-((benzyloxy)methyl)-5-methyl-4-(((2S,3R,4S,5R)-3,4,5-trimethoxytetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)acetaldehyde
• CAS: 1035662-61-3
• 化学式: C₂₄H₃₆O₈
• 分子量: 452.545
• InChiKey: CPLRZECVICIIBV-ILYHWOFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.37
• 重原子数：
  32.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  81.68
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2-((2S,4S,5R,6R)-6-((benzyloxy)methyl)-5-methyl-4-(((2S,3R,4S,5R)-3,4,5-trimethoxytetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)acetaldehyde 、 丙炔 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 以59%的产率得到(S)-1-((2R,4S,5R,6R)-6-((benzyloxy)methyl)-5-methyl-4-(((2S,3R,4S,5R)-3,4,5-trimethoxytetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)pent-3-yn-2-ol
  参考文献：
  名称：

  Total synthesis of clavosolide A

  摘要：

  For the total synthesis of (-)-clavosolide A described herein, a Schmidt glycosidation reaction was used to attach the sugar moiety at an early stage in the synthesis to the 4-hydroxy group of the substituted tetrahydropyran unit of the molecule, which itself was built following a Ti(III)-mediated method developed by us earlier, and at the end, it was the Yamaguchi reaction that was successfully employed for the cyclodimerization of the two halves of the molecule leading to its total synthesis. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.03.039
• 作为产物：
  描述：

  2-((2R,4S,5R,6R)-6-((benzyloxy)methyl)-5-methyl-4-(((2S,3R,4S,5R)-3,4,5-trimethoxytetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)ethan-1-ol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以96%的产率得到2-((2S,4S,5R,6R)-6-((benzyloxy)methyl)-5-methyl-4-(((2S,3R,4S,5R)-3,4,5-trimethoxytetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)acetaldehyde
  参考文献：
  名称：

  Total synthesis of clavosolide A

  摘要：

  For the total synthesis of (-)-clavosolide A described herein, a Schmidt glycosidation reaction was used to attach the sugar moiety at an early stage in the synthesis to the 4-hydroxy group of the substituted tetrahydropyran unit of the molecule, which itself was built following a Ti(III)-mediated method developed by us earlier, and at the end, it was the Yamaguchi reaction that was successfully employed for the cyclodimerization of the two halves of the molecule leading to its total synthesis. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.03.039