(5S, 6R, 12S, 14S)-14-(benzyloxy)-12,16-bis((tert-dimethylsilyl)oxy)-6-hydroxy-5-methylhexadecan-8-one | 1337552-73-4

• 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: (5S, 6R, 12S, 14S)-14-(benzyloxy)-12,16-bis((tert-dimethylsilyl)oxy)-6-hydroxy-5-methylhexadecan-8-one
• 英文别名: (5S,6R,12S,14S)-12,16-bis[[tert-butyl(dimethyl)silyl]oxy]-6-hydroxy-5-methyl-14-phenylmethoxyhexadecan-8-one
• CAS: 1337552-73-4
• 化学式: C₃₆H₆₈O₅Si₂
• 分子量: 637.104
• InChiKey: GNTLDFLKVDUSSV-TUONYQKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.08
• 重原子数：
  43
• 可旋转键数：
  23
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (5S, 6R, 12S, 14S)-14-(benzyloxy)-12,16-bis((tert-dimethylsilyl)oxy)-6-hydroxy-5-methylhexadecan-8-one 在 sodium tetrahydroborate 、 二乙基甲氧基硼烷 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.0h， 以90%的产率得到(5S,6R,8R,12S,14S)-14-(benzyloxy)-12,16-bis((tert-butyldimethylsilyl)oxy)-5-methylhexadecane-6,8-diol
  参考文献：
  名称：

  Convergent enantioselective syntheses of two potential C25-C40 subunits of (-)-caylobolide A

  摘要：

  The convergent syntheses of two possible diastereomers of the C25-C40 subunit resident in (-)-caylobolide A have been accomplished. The key reaction featured a chemoselective Ru-catalyzed cross-metathesis between a fully elaborated type I and two functionalized type II alpha,beta-unsaturated ketones. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.07.105
• 作为产物：
  描述：

  (5R, 11S, 13S)-13-(benzyloxy)-11-((tert-butyldimethylsilyl)oxy)-3,3-diethyl-5-((S)-hexan-2-yl)-17,17,18,18-tetramethyl-4,16-dioxa-3,17-disilanonadecan-7-one 在 甲醇 、 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以80%的产率得到(5S, 6R, 12S, 14S)-14-(benzyloxy)-12,16-bis((tert-dimethylsilyl)oxy)-6-hydroxy-5-methylhexadecan-8-one
  参考文献：
  名称：

  Convergent enantioselective syntheses of two potential C25-C40 subunits of (-)-caylobolide A

  摘要：

  The convergent syntheses of two possible diastereomers of the C25-C40 subunit resident in (-)-caylobolide A have been accomplished. The key reaction featured a chemoselective Ru-catalyzed cross-metathesis between a fully elaborated type I and two functionalized type II alpha,beta-unsaturated ketones. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.07.105