(2S,3S,6R)-7-[tert-butyl(dimethyl)silyl]oxy-1-[tert-butyl(diphenyl)silyl]oxy-2,6-dimethylhept-4-yn-3-ol | 944051-95-0

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2S,3S,6R)-7-[tert-butyl(dimethyl)silyl]oxy-1-[tert-butyl(diphenyl)silyl]oxy-2,6-dimethylhept-4-yn-3-ol
• CAS: 944051-95-0
• 化学式: C₃₁H₄₈O₃Si₂
• 分子量: 524.891
• InChiKey: JDHMNWIPAJEXGH-UWPQIUOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.22
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3S,6R)-7-[tert-butyl(dimethyl)silyl]oxy-1-[tert-butyl(diphenyl)silyl]oxy-2,6-dimethylhept-4-yn-3-ol 在 吡啶 、 2,6-二甲基吡啶 、 sodium tetrahydroborate 、 氢氟酸 、 nickel diacetate 、 乙二胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 6.17h， 生成 C₃₁H₅₀O₃Si₂
  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：

  (S)-3-(tert-butyldimethylsilyloxy)-2-methylpropionic acid methyl ester 在 锂硼氢 、 草酰氯 、 二甲基亚砜 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 40.25h， 生成 (2S,3S,6R)-7-[tert-butyl(dimethyl)silyl]oxy-1-[tert-butyl(diphenyl)silyl]oxy-2,6-dimethylhept-4-yn-3-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

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.