(3S,4R,5S,6R)-9-(benzyloxy)-4,6-dimethylnonane-1,3,5-triol | 944052-10-2

• 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: (3S,4R,5S,6R)-9-(benzyloxy)-4,6-dimethylnonane-1,3,5-triol
• CAS: 944052-10-2
• 化学式: C₁₈H₃₀O₄
• 分子量: 310.434
• InChiKey: FDOQHVJAOUICGU-LMSBXDPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.36
• 重原子数：
  22.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  69.92
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3S,4R,5S,6R)-9-(benzyloxy)-4,6-dimethylnonane-1,3,5-triol 在 bis-triphenylphosphine-palladium(II) chloride 吡啶 、 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 sodium hydroxide 、 正丁基锂 、 氢氟酸 、 三氧化硫 、 三正丁基氢锡 、 二异丁基氢化铝 、 二甲基亚砜 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 9.17h， 生成 (2E,4E,7S,8R,9S,10R)-13-(benzyloxy)-7,9-bis((tert-butyldimethylsilyl)oxy)-2-iodo-4,8,10-trimethyltrideca-2,4-dien-1-ol
  参考文献：
  名称：

  Studies directed towards the total synthesis of lycoperdinosides: stereoselective construction of the C1–C9 and C10–C21 segments of the molecules

  摘要：

  The three chiral centres of the C1-C9 moiety of the six-membered lactone glycosides, lycoperdinosides A and B, have been derived from a common starting material containing a single chiral centre. In contrast, the C10-C21 segment of these molecules has been synthesized using, as key steps, a highly stereoselective aldol reaction, a Ti(III)-mediated opening of a trisubstituted epoxy alcohol and an efficient directed hydrostannylation of a suitably substituted internal alkyne. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.04.016
• 作为产物：
  描述：

  (4R)-4-[(4S,5R,6S)-2,2,5-trimethyl-6-(2-trityloxyethyl)-1,3-dioxan-4-yl]pentan-1-ol 在 sodium hexamethyldisilazane 、 三氟乙酸 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 2.0h， 生成 (3S,4R,5S,6R)-9-(benzyloxy)-4,6-dimethylnonane-1,3,5-triol
  参考文献：
  名称：

  Studies directed towards the total synthesis of lycoperdinosides: stereoselective construction of the C1–C9 and C10–C21 segments of the molecules

  摘要：

  The three chiral centres of the C1-C9 moiety of the six-membered lactone glycosides, lycoperdinosides A and B, have been derived from a common starting material containing a single chiral centre. In contrast, the C10-C21 segment of these molecules has been synthesized using, as key steps, a highly stereoselective aldol reaction, a Ti(III)-mediated opening of a trisubstituted epoxy alcohol and an efficient directed hydrostannylation of a suitably substituted internal alkyne. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.04.016