[(4R)-4-[tert-butyl(diphenyl)silyl]oxypentyl] 4-methylbenzenesulfonate | 189163-29-9

• 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: [(4R)-4-[tert-butyl(diphenyl)silyl]oxypentyl] 4-methylbenzenesulfonate
• CAS: 189163-29-9
• 化学式: C₂₈H₃₆O₄SSi
• 分子量: 496.743
• InChiKey: RWWYMQNIIRUHLI-XMMPIXPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.45
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(4R)-4-[tert-butyl(diphenyl)silyl]oxypentyl] 4-methylbenzenesulfonate 在 咪唑 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 正丁基锂 、 草酰氯 、 四丁基氟化铵 、 4-甲基苯磺酸吡啶 、 sodium hydride 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 二乙二醇二甲醚 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 109.0h， 生成 benzyl (2E,4E,7S,10E,15R)-15-[tert-butyl(diphenyl)silyl]oxy-7-methoxy-2-methylhexadeca-2,4,10-trienoate
  参考文献：
  名称：

  Total Synthesis of Dolatrienoic Acid:  A Subunit of Dolastatin 14

  摘要：

  The (7R,15R)- and (7S,15R)-diastereomers of dolatrienoic acid were synthesized using a convergent strategy. Fragment C5-C9 was obtained through enantiodifferentiation of racemic pentane-1,3,5-triol as the key step, fixing the chirality at C7 of fragments 4 and ent-4. The chirality at C15 of the fragment C10-C16 was introduced from L-glutamic acid. Coupling of these two fragments led to the aldehydes (7R,15R)- and (7S,15R)-2 which were homologated by Horner-Wadsworth-Emmons condensation to give (7R,15R)- and (7S,15R)-dolatrienoic acids.

  DOI：

  10.1021/jo962217a
• 作为产物：
  描述：

  (R)-1-<(triphenylmethyl)oxy>pentan-4-ol 在 咪唑 、 4-二甲氨基吡啶 、 4-甲基苯磺酸吡啶 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成 [(4R)-4-[tert-butyl(diphenyl)silyl]oxypentyl] 4-methylbenzenesulfonate
  参考文献：
  名称：

  Total Synthesis of Dolatrienoic Acid:  A Subunit of Dolastatin 14

  摘要：

  The (7R,15R)- and (7S,15R)-diastereomers of dolatrienoic acid were synthesized using a convergent strategy. Fragment C5-C9 was obtained through enantiodifferentiation of racemic pentane-1,3,5-triol as the key step, fixing the chirality at C7 of fragments 4 and ent-4. The chirality at C15 of the fragment C10-C16 was introduced from L-glutamic acid. Coupling of these two fragments led to the aldehydes (7R,15R)- and (7S,15R)-2 which were homologated by Horner-Wadsworth-Emmons condensation to give (7R,15R)- and (7S,15R)-dolatrienoic acids.

  DOI：

  10.1021/jo962217a

文献信息

• Total Synthesis of Dolatrienoic Acid:  A Subunit of Dolastatin 14
  作者：Sylvie Mouné,、Gilles Niel、Magali Busquet、Ian Eggleston、Patrick Jouin

  DOI：10.1021/jo962217a

  日期：1997.5.1

  The (7R,15R)- and (7S,15R)-diastereomers of dolatrienoic acid were synthesized using a convergent strategy. Fragment C5-C9 was obtained through enantiodifferentiation of racemic pentane-1,3,5-triol as the key step, fixing the chirality at C7 of fragments 4 and ent-4. The chirality at C15 of the fragment C10-C16 was introduced from L-glutamic acid. Coupling of these two fragments led to the aldehydes (7R,15R)- and (7S,15R)-2 which were homologated by Horner-Wadsworth-Emmons condensation to give (7R,15R)- and (7S,15R)-dolatrienoic acids.