(+/-)-methanesulfonic acid 1-(6-methoxy-3,5-dimethyl-4-oxo-4H-pyran-2-yl)ethyl ester | 760998-27-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (+/-)-methanesulfonic acid 1-(6-methoxy-3,5-dimethyl-4-oxo-4H-pyran-2-yl)ethyl ester
• 英文别名: 1-(6-Methoxy-3,5-dimethyl-4-oxopyran-2-yl)ethyl methanesulfonate
• CAS: 760998-27-4
• 化学式: C₁₁H₁₆O₆S
• 分子量: 276.31
• InChiKey: RXYIGTXFYYGMPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  87.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+/-)-methanesulfonic acid 1-(6-methoxy-3,5-dimethyl-4-oxo-4H-pyran-2-yl)ethyl ester 在 sodium hydride 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.17h， 生成 cyercene A
  参考文献：
  名称：

  Total synthesis of cyercene A and the biomimetic synthesis of (±)-9,10-deoxytridachione and (±)-ocellapyrone A

  摘要：

  This paper summarises our detailed study towards the biomimetic synthesis of the complex polypropionate derived natural product (+/-)-9,10-deoxytridachione. A previous study based on the elaboration of functionalised gamma-pyrones allowed us to synthesise cyercene A. The same efficient methodology has been applied for the elaboration of a more complex fully conjugated gamma-pyrone polyene. Our approach centred on a key tandem Suzuki-coupling/electrocyclisation reaction, which supports a possible biosynthetic pathway for this class of natural products. A related compound was obtained during our studies, which we identified as the correct structure of ocellapyrone A. (C) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2007.03.057
• 作为产物：
  描述：

  4-甲基庚烷-3,5-二酮 在 lithium carbonate 、 三乙胺 、 lithium hexamethyldisilazane 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 91.17h， 生成 (+/-)-methanesulfonic acid 1-(6-methoxy-3,5-dimethyl-4-oxo-4H-pyran-2-yl)ethyl ester
  参考文献：
  名称：

  Total synthesis of cyercene A and the biomimetic synthesis of (±)-9,10-deoxytridachione and (±)-ocellapyrone A

  摘要：

  This paper summarises our detailed study towards the biomimetic synthesis of the complex polypropionate derived natural product (+/-)-9,10-deoxytridachione. A previous study based on the elaboration of functionalised gamma-pyrones allowed us to synthesise cyercene A. The same efficient methodology has been applied for the elaboration of a more complex fully conjugated gamma-pyrone polyene. Our approach centred on a key tandem Suzuki-coupling/electrocyclisation reaction, which supports a possible biosynthetic pathway for this class of natural products. A related compound was obtained during our studies, which we identified as the correct structure of ocellapyrone A. (C) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2007.03.057

文献信息

• An efficient synthesis of cyercene A
  作者：John E. Moses、Jack E. Baldwin、Robert M. Adlington

  DOI：10.1016/j.tetlet.2004.06.125

  日期：2004.8

  An efficient approach to the total synthesis of the marine derived polypropionate cyercene A is described. A key feature of the synthesis is the development of methodology for the diastereoselective Wadsworth-Emmons type condensation of a functionalised gamma-pyrone unit. (C) 2004 Elsevier Ltd. All rights reserved.