(4S,5R,6R)-7-Benzyloxy-5-methoxymethoxy-4,6-dimethyl-heptan-3-one | 156628-33-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4S,5R,6R)-7-Benzyloxy-5-methoxymethoxy-4,6-dimethyl-heptan-3-one
• 英文别名: (4S,5R,6R)-5-(methoxymethoxy)-4,6-dimethyl-7-phenylmethoxyheptan-3-one
• CAS: 156628-33-0
• 化学式: C₁₈H₂₈O₄
• 分子量: 308.418
• InChiKey: MVRZPUICEDLXJE-IIDMSEBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 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：

  (4S,5R,6R)-7-Benzyloxy-5-methoxymethoxy-4,6-dimethyl-heptan-3-one 在 吡啶 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 9-borabicyclo[3.3.1]nonane dimer 、 双氧水 、 lithium iodide 、 lithium diisopropyl amide 作用下， 生成 Toluene-4-sulfonic acid (4R,5S,6R,7R,8R)-9-benzyloxy-5-hydroxy-7-methoxymethoxy-4,6,8-trimethyl-nonyl ester
  参考文献：
  名称：

  An alkylative strategy to the C-13 to C-21 sector of discodermolide

  摘要：

  An approach to the C-13 to C-21 sector of the immunosuppressive marine natural product discodermolide (1) is described. The C-15 to C-16 bond is formed by diastereoselective alkylation of a ketone enolate. Either diastereomer of allkylation Can be obtained by selecting the appropriate counter ion. The C-16 to C-21 subunit is prepared in two steps from 11.

  DOI：

  10.1016/s0040-4039(00)76205-8
• 作为产物：
  描述：

  (-)-(S)-1-苄氧基-3-羟基-2-甲基丙烷 在 草酰氯 、 lithium bis(dimethylphenylsilyl)amide 、 二乙基异丙基胺 、 四丁基碘化铵 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 (4S,5R,6R)-7-Benzyloxy-5-methoxymethoxy-4,6-dimethyl-heptan-3-one
  参考文献：
  名称：

  An alkylative strategy to the C-13 to C-21 sector of discodermolide

  摘要：

  An approach to the C-13 to C-21 sector of the immunosuppressive marine natural product discodermolide (1) is described. The C-15 to C-16 bond is formed by diastereoselective alkylation of a ketone enolate. Either diastereomer of allkylation Can be obtained by selecting the appropriate counter ion. The C-16 to C-21 subunit is prepared in two steps from 11.

  DOI：

  10.1016/s0040-4039(00)76205-8

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.
• An alkylative strategy to the C-13 to C-21 sector of discodermolide
  作者：Ge Yang、David C. Myles

  DOI：10.1016/s0040-4039(00)76205-8

  日期：1994.2

  An approach to the C-13 to C-21 sector of the immunosuppressive marine natural product discodermolide (1) is described. The C-15 to C-16 bond is formed by diastereoselective alkylation of a ketone enolate. Either diastereomer of allkylation Can be obtained by selecting the appropriate counter ion. The C-16 to C-21 subunit is prepared in two steps from 11.