(S)-6-[(E)-3-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)allyloxy]-5-methylhexanoic acid ethyl ester | 387834-63-1

• 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: (S)-6-[(E)-3-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)allyloxy]-5-methylhexanoic acid ethyl ester
• 英文别名: ethyl (5S)-6-[(E)-3-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)prop-2-enoxy]-5-methylhexanoate
• CAS: 387834-63-1
• 化学式: C₁₇H₃₁BO₅
• 分子量: 326.241
• InChiKey: NNEJASBGZFLVPP-VSGCLNPGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.03
• 重原子数：
  23
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  乙基溴化镁 、 (1R,5R)-(Z)-3-bromomethylene-5-(tert-butyldimethyl-silanyloxy)cyclohexanol 、 (S)-6-[(E)-3-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)allyloxy]-5-methylhexanoic acid ethyl ester 以93%的产率得到(1R,3R)-5-[(S)-(E)-4-(6-ethyl-6-hydroxy-2-methyloctyloxy)but-2-enylidene]cyclohexane-1,3-diol
  参考文献：
  名称：

  Novel Synthetic Approach to 19-nor-1α,25-Dihydroxyvitamin D₃ and Its Derivatives by Suzuki−Miyaura Coupling in Solution and on Solid Support

  摘要：

  [GRAPHICS]19-nor-1 alpha ,25-Dihydroxyvitamin D-3 was synthesized by the Suzuki-Miyaura coupling of the A-ring intermediate 3, which was efficiently prepared from readily available 5-(tert butyldimethylsilyl)oxycyclohex-2-enone (5), with the boronate compound of the C,D-ring portion. The method could be applied to a solid-phase synthesis to prepare the des-C,D derivatives of 19-nor-1 alpha ,25-dihydroxyvitamin D-3.

  DOI：

  10.1021/ol016908r
• 作为产物：
  描述：

  (S)-5-methyl-6-(prop-2-ynyloxy)hexanoic acid ethyl ester 在 Pinene 、 dimethyl sulfide borane 、 乙醛 作用下， 以 四氢呋喃 为溶剂， 生成 (S)-6-[(E)-3-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)allyloxy]-5-methylhexanoic acid ethyl ester
  参考文献：
  名称：

  Novel Synthetic Approach to 19-nor-1α,25-Dihydroxyvitamin D₃ and Its Derivatives by Suzuki−Miyaura Coupling in Solution and on Solid Support

  摘要：

  [GRAPHICS]19-nor-1 alpha ,25-Dihydroxyvitamin D-3 was synthesized by the Suzuki-Miyaura coupling of the A-ring intermediate 3, which was efficiently prepared from readily available 5-(tert butyldimethylsilyl)oxycyclohex-2-enone (5), with the boronate compound of the C,D-ring portion. The method could be applied to a solid-phase synthesis to prepare the des-C,D derivatives of 19-nor-1 alpha ,25-dihydroxyvitamin D-3.

  DOI：

  10.1021/ol016908r