(Z)-(4R,5S,6R)-7-Benzyloxy-2,4,6-trimethyl-hept-2-ene-1,5-diol | 153628-61-6

• 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: (Z)-(4R,5S,6R)-7-Benzyloxy-2,4,6-trimethyl-hept-2-ene-1,5-diol
• 英文别名: (Z,4R,5S,6R)-2,4,6-trimethyl-7-phenylmethoxyhept-2-ene-1,5-diol
• CAS: 153628-61-6
• 化学式: C₁₇H₂₆O₃
• 分子量: 278.392
• InChiKey: KLUNAZANKRCNLD-WJAMWVSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-(4R,5S,6R)-7-Benzyloxy-2,4,6-trimethyl-hept-2-ene-1,5-diol 在 吡啶 、 2,6-二甲基吡啶 、 甲基三苯氧基碘磷 、 sodium hexamethyldisilazane 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (4S)-4-benzyl-3-[(Z,2R,6R,7S,8R)-2,4,6,8-tetramethyl-9-phenylmethoxy-7-tri(propan-2-yl)silyloxynon-4-enoyl]-1,3-oxazolidin-2-one
  参考文献：
  名称：

  The synthesis of a C9-C17, fragment of discodermolide

  摘要：

  The asymmetric synthesis of a synthetically useful fragment corresponding to the C-9-C-17 region of the immunosuppressant lactone discodermolide is reported. The route incorporates the use of an unsaturated lactone to provide a trisubstituted olefin with absolute control of geometry.

  DOI：

  10.1016/s0040-4039(00)61480-6
• 作为产物：
  描述：

  (R)-1-((R)-4-benzyl-2-oxooxazolidin-3-yl)-2-methylpentane-1,3-dione 在 lithium hydroxide 、 tin(II) trifluoromethanesulfonate 、 双氧水 、 二异丁基氢化铝 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (Z)-(4R,5S,6R)-7-Benzyloxy-2,4,6-trimethyl-hept-2-ene-1,5-diol
  参考文献：
  名称：

  The synthesis of a C9-C17, fragment of discodermolide

  摘要：

  The asymmetric synthesis of a synthetically useful fragment corresponding to the C-9-C-17 region of the immunosuppressant lactone discodermolide is reported. The route incorporates the use of an unsaturated lactone to provide a trisubstituted olefin with absolute control of geometry.

  DOI：

  10.1016/s0040-4039(00)61480-6

文献信息

• The synthesis of the C-9 to C-21 sector of discodermolide: An efficient route to the C13–14 Z-trisubstituted alkene
  作者：Ge Yang、David C. Myles

  DOI：10.1016/s0040-4039(00)77155-3

  日期：1994.4

  The synthesis of the C-9 to C-21 sector of the immunosuppressive marine natural product discodermolide is described. The C-9 to C-15 subunit is synthesized in five steps from aldehyde 5 using the diene aldehyde cyclocondensation reaction. Diastereoselective alkylation of the previously synthesized C-16 to C-21 subunit by a suitably functionalized C-9 to C-15 synthon (3) leads to the C-9 to C-21 sector of discodermolide.
• The synthesis of a C9-C17, fragment of discodermolide
  作者：Philip L. Evans、Julian M.C. Golec、Roger J. Gillespie

  DOI：10.1016/s0040-4039(00)61480-6

  日期：1993.12

  The asymmetric synthesis of a synthetically useful fragment corresponding to the C-9-C-17 region of the immunosuppressant lactone discodermolide is reported. The route incorporates the use of an unsaturated lactone to provide a trisubstituted olefin with absolute control of geometry.