(4R,5R)-4,5-bis-(tert-butyldimethylsilanyloxy)heptadecanoic acid ethyl ester | 1107639-72-4

• 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: (4R,5R)-4,5-bis-(tert-butyldimethylsilanyloxy)heptadecanoic acid ethyl ester
• 英文别名: ethyl (4R,5R)-4,5-bis[[tert-butyl(dimethyl)silyl]oxy]heptadecanoate
• CAS: 1107639-72-4
• 化学式: C₃₁H₆₆O₄Si₂
• 分子量: 559.034
• InChiKey: QGNDGRPVKBCHRO-VSGBNLITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.42
• 重原子数：
  37
• 可旋转键数：
  23
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R,5R)-4,5-bis-(tert-butyldimethylsilanyloxy)heptadecanoic acid ethyl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以74%的产率得到(5R)-5-[(1R)-1-羟基十三烷基]四氢呋喃-2-酮
  参考文献：
  名称：

  Synthesis of γ-lactones by desymmetrization. A synthesis of (−)-muricatacin

  摘要：

  A short synthesis of the natural potent cytotoxic agent (-)-muricatacin 1 and related unsaturated lactones from a versatile common intermediate, dienedioate 2, derived from D-mannitol or tartaric acid, is described. The strategy depends upon the desymmetrization of 7 by dihydroxylation and elaboration of the hydroxy alkyl sidechain. A route to unsaturated lactones is also described using a cis selective Wittig reaction. Since the enantiomers of 2 are available from the corresponding tartaric acids, this method provides access to both enantiomers of the described compounds and a wide range of derivatives. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.10.020
• 作为产物：
  描述：

  (4R,5R,2E,6Z)-4,5-bis-(tert-butyldimethylsilanyloxy)heptadeca-2,6-dienoic acid ethyl ester 在 10% Pd/C 、 氢气 作用下， 以 乙醇 为溶剂， 以95%的产率得到(4R,5R)-4,5-bis-(tert-butyldimethylsilanyloxy)heptadecanoic acid ethyl ester
  参考文献：
  名称：

  Synthesis of γ-lactones by desymmetrization. A synthesis of (−)-muricatacin

  摘要：

  A short synthesis of the natural potent cytotoxic agent (-)-muricatacin 1 and related unsaturated lactones from a versatile common intermediate, dienedioate 2, derived from D-mannitol or tartaric acid, is described. The strategy depends upon the desymmetrization of 7 by dihydroxylation and elaboration of the hydroxy alkyl sidechain. A route to unsaturated lactones is also described using a cis selective Wittig reaction. Since the enantiomers of 2 are available from the corresponding tartaric acids, this method provides access to both enantiomers of the described compounds and a wide range of derivatives. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.10.020

文献信息

• Synthesis of γ-lactones by desymmetrization. A synthesis of (−)-muricatacin
  作者：M. Teresa Barros、M. Adilia Januario Charmier、Christopher D. Maycock、Thierry Michaud

  DOI：10.1016/j.tet.2008.10.020

  日期：2009.1

  A short synthesis of the natural potent cytotoxic agent (-)-muricatacin 1 and related unsaturated lactones from a versatile common intermediate, dienedioate 2, derived from D-mannitol or tartaric acid, is described. The strategy depends upon the desymmetrization of 7 by dihydroxylation and elaboration of the hydroxy alkyl sidechain. A route to unsaturated lactones is also described using a cis selective Wittig reaction. Since the enantiomers of 2 are available from the corresponding tartaric acids, this method provides access to both enantiomers of the described compounds and a wide range of derivatives. (C) 2008 Elsevier Ltd. All rights reserved.