(2R,6S)-6-[(4S)-4-benzyloxy-3,3-dimethyl-2-oxohex-5-enyl]-2-[(tert-butyldiphenylsilyloxy)methyl]-4-methylenetetrahydropyran | 1314809-09-0

• 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: (2R,6S)-6-[(4S)-4-benzyloxy-3,3-dimethyl-2-oxohex-5-enyl]-2-[(tert-butyldiphenylsilyloxy)methyl]-4-methylenetetrahydropyran
• 英文别名: (4S)-1-[(2S,6R)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-methylideneoxan-2-yl]-3,3-dimethyl-4-phenylmethoxyhex-5-en-2-one
• CAS: 1314809-09-0
• 化学式: C₃₈H₄₈O₄Si
• 分子量: 596.882
• InChiKey: SHPVIMHIUKMIKR-YDZJUXTKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.42
• 重原子数：
  43
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,6S)-6-[(4S)-4-benzyloxy-3,3-dimethyl-2-oxohex-5-enyl]-2-[(tert-butyldiphenylsilyloxy)methyl]-4-methylenetetrahydropyran 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以95%的产率得到(2R,6S)-6-[(4S)-4-benzyloxy-3,3-dimethyl-2-oxohex-5-enyl]-2-[(tert-butyldiphenylsilyloxy)methyl]-4-methyl-4,1''-epoxytetrahydropyran
  参考文献：
  名称：

  Synthesis of 2,6-cis-disubstituted 4-methylenetetrahydropyrans by oxy-Michael addition

  摘要：

  The combination of an 'ene' reaction between a 2-(2-trialkylsilyloxyalkyl)prop-2-enyl(trimethyl)silane and an alk-1-yn-3-one mediated by zinc(II) iodide, and an intramolecular oxy-Michael reaction, provides an efficient synthesis of cis-2,6-disubstituted 4-methylenetetrahydropyrans of interest in the context of a synthesis of bryostatins. The stereoselective formation of (E)-vinylsilanes in the 'ene' reaction is of interest. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.113
• 作为产物：
  描述：

  (3S)-3-(benzyloxy)-2,2-dimethyl-4-penten-1-ol 在 咪唑 、 草酰氯 、 氢氟酸 、 水 、 戴斯-马丁氧化剂 、 二甲基亚砜 、 zinc(II) iodide 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 82.0h， 生成 (2R,6R)-6-[(4S)-4-benzyloxy-3,3-dimethyl-2-oxohex-5-enyl]-2-[(tert-butyldiphenylsilyloxy)methyl]-4-methylidenetetrahydropyran 、 (2R,6S)-6-[(4S)-4-benzyloxy-3,3-dimethyl-2-oxohex-5-enyl]-2-[(tert-butyldiphenylsilyloxy)methyl]-4-methylenetetrahydropyran
  参考文献：
  名称：

  Synthesis of 2,6-cis-disubstituted 4-methylenetetrahydropyrans by oxy-Michael addition

  摘要：

  The combination of an 'ene' reaction between a 2-(2-trialkylsilyloxyalkyl)prop-2-enyl(trimethyl)silane and an alk-1-yn-3-one mediated by zinc(II) iodide, and an intramolecular oxy-Michael reaction, provides an efficient synthesis of cis-2,6-disubstituted 4-methylenetetrahydropyrans of interest in the context of a synthesis of bryostatins. The stereoselective formation of (E)-vinylsilanes in the 'ene' reaction is of interest. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.113

文献信息

• Synthesis of 2,6-cis-disubstituted 4-methylenetetrahydropyrans by oxy-Michael addition
  作者：Duncan Gill、Nicholas H. Taylor、Eric J. Thomas

  DOI：10.1016/j.tet.2011.03.113

  日期：2011.7

  The combination of an 'ene' reaction between a 2-(2-trialkylsilyloxyalkyl)prop-2-enyl(trimethyl)silane and an alk-1-yn-3-one mediated by zinc(II) iodide, and an intramolecular oxy-Michael reaction, provides an efficient synthesis of cis-2,6-disubstituted 4-methylenetetrahydropyrans of interest in the context of a synthesis of bryostatins. The stereoselective formation of (E)-vinylsilanes in the 'ene' reaction is of interest. (C) 2011 Elsevier Ltd. All rights reserved.