2-[(4S,5R,6S)-6-[(2R)-1-[tert-butyl(diphenyl)silyl]oxypropan-2-yl]-2,2,5-trimethyl-1,3-dioxan-4-yl]ethanol | 944052-05-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[(4S,5R,6S)-6-[(2R)-1-[tert-butyl(diphenyl)silyl]oxypropan-2-yl]-2,2,5-trimethyl-1,3-dioxan-4-yl]ethanol
• CAS: 944052-05-5
• 化学式: C₂₈H₄₂O₄Si
• 分子量: 470.725
• InChiKey: OPZJYPJIRNCNSM-PWGHIRGTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.74
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[(4S,5R,6S)-6-[(2R)-1-[tert-butyl(diphenyl)silyl]oxypropan-2-yl]-2,2,5-trimethyl-1,3-dioxan-4-yl]ethanol 在 吡啶 、 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 锂硼氢 、 正丁基锂 、 草酰氯 、 氢氟酸 、 三氧化硫 、 四丁基氟化铵 、 sodium hexamethyldisilazane 、 二异丁基氢化铝 、 二甲基亚砜 、 三乙胺 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 27.92h， 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：

  tert-butyl-diphenyl-[(2R)-2-[(4S,5R,6S)-2,2,5-trimethyl-6-(2-phenylmethoxyethyl)-1,3-dioxan-4-yl]propoxy]silane 在 氨 、 lithium 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以78%的产率得到2-[(4S,5R,6S)-6-[(2R)-1-[tert-butyl(diphenyl)silyl]oxypropan-2-yl]-2,2,5-trimethyl-1,3-dioxan-4-yl]ethanol
  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.