(S)-1-((4aR,6S,7R,8aS)-2,2-di-tert-butyl-7-hydroxyhexahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl)penta-3,4-dien-2-yl acetate | 1456889-18-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子
• 英文名称: (S)-1-((4aR,6S,7R,8aS)-2,2-di-tert-butyl-7-hydroxyhexahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl)penta-3,4-dien-2-yl acetate
• CAS: 1456889-18-1
• 化学式: C₂₁H₃₆O₆Si
• 分子量: 412.599
• InChiKey: OOUQZGYJPARWHJ-ZSXDVEMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.63
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  74.22
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (S)-1-((4aR,6S,7R,8aS)-2,2-di-tert-butyl-7-hydroxyhexahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl)penta-3,4-dien-2-yl acetate 在 silver perchlorate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 20.0h， 以71%的产率得到(4aR,5aS,7S,8S,9aR,10aS)-2,2-di-tert-butyl-8-vinyloctahydro-4H-pyrano[2',3':5,6]pyrano[3,2-d][1,3,2]dioxasilin-7-yl acetate
  参考文献：
  名称：

  Synthesis of fused tetrahydropyrans by hydroalkoxylation of δ-hydroxy allenes

  摘要：

  Fused tetrahydropyrans were synthesized by silver(l)- and mercury(II)-mediated intramolecular hydroalkoxylations of delta-hydroxy allenes installed on a tetrahydropyran template. Cyclization of simple allenes was promoted by silver perchlorate to afford vinyl-substituted trans-fused bis-tetrahydropyrans, whereas cyclization of methyl-substituted allenes at the internal allenic carbon atom was achieved more effectively with a catalytic amount of mercuric triflate rather than with silver salts. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.08.026
• 作为产物：
  描述：

  (4aR,6S,7R,8aS)-2,2-di-tert-butyl-7-((triethylsilyl)oxy)-6-vinylhexahydropyrano[3,2-d][1,3,2]dioxasiline 在 吡啶 、 chromium dichloride 、 甲醇 、 4-二甲氨基吡啶 、 双氧水 、 sodium methylate 、 4-甲基苯磺酸吡啶 、 potassium carbonate 、 戴斯-马丁氧化剂 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 27.25h， 生成 (S)-1-((4aR,6S,7R,8aS)-2,2-di-tert-butyl-7-hydroxyhexahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl)penta-3,4-dien-2-yl acetate
  参考文献：
  名称：

  Synthesis of fused tetrahydropyrans by hydroalkoxylation of δ-hydroxy allenes

  摘要：

  Fused tetrahydropyrans were synthesized by silver(l)- and mercury(II)-mediated intramolecular hydroalkoxylations of delta-hydroxy allenes installed on a tetrahydropyran template. Cyclization of simple allenes was promoted by silver perchlorate to afford vinyl-substituted trans-fused bis-tetrahydropyrans, whereas cyclization of methyl-substituted allenes at the internal allenic carbon atom was achieved more effectively with a catalytic amount of mercuric triflate rather than with silver salts. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.08.026