(4S,5R,6S)-2,2,5-trimethyl-4-[(2R)-5-phenylmethoxypentan-2-yl]-6-(2-trityloxyethyl)-1,3-dioxane | 944052-09-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (4S,5R,6S)-2,2,5-trimethyl-4-[(2R)-5-phenylmethoxypentan-2-yl]-6-(2-trityloxyethyl)-1,3-dioxane
• CAS: 944052-09-9
• 化学式: C₄₀H₄₈O₄
• 分子量: 592.819
• InChiKey: CCXQZRLJMDMTSZ-RGXXHLTKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  44
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S,5R,6S)-2,2,5-trimethyl-4-[(2R)-5-phenylmethoxypentan-2-yl]-6-(2-trityloxyethyl)-1,3-dioxane 在 吡啶 、 2,6-二甲基吡啶 、 正丁基锂 、 氢氟酸 、 三氧化硫 、 二异丁基氢化铝 、 二甲基亚砜 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 叔丁醇 为溶剂， 反应 9.92h， 生成 (7S,8R,9S,10R,E)-13-(benzyloxy)-7,9-bis((tert-butyldimethylsilyl)oxy)-4,8,10-trimethyltridec-4-en-2-yn-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：

  在 锂硼氢 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 (4S,5R,6S)-2,2,5-trimethyl-4-[(2R)-5-phenylmethoxypentan-2-yl]-6-(2-trityloxyethyl)-1,3-dioxane
  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

文献信息

• Studies directed towards the total synthesis of lycoperdinosides: stereoselective construction of the C1–C9 and C10–C21 segments of the molecules
  作者：Tushar Kanti Chakraborty、Rajib Kumar Goswami、Midde Sreekanth

  DOI：10.1016/j.tetlet.2007.04.016

  日期：2007.6

  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.