(2RS,7S)-7-(tert-butyldimethyl-silanyloxy)-7-[(4R)-2,2-dimethyl-1,3-dioxalan-4-yl]-4-heptene-1,2-diol | 444885-15-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2RS,7S)-7-(tert-butyldimethyl-silanyloxy)-7-[(4R)-2,2-dimethyl-1,3-dioxalan-4-yl]-4-heptene-1,2-diol
• 英文别名: (Z,7S)-7-[tert-butyl(dimethyl)silyl]oxy-7-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]hept-4-ene-1,2-diol
• CAS: 444885-15-8
• 化学式: C₁₈H₃₆O₅Si
• 分子量: 360.566
• InChiKey: KFZGYMWPHWENOW-YLIOYJPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.22
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2RS,7S)-7-(tert-butyldimethyl-silanyloxy)-7-[(4R)-2,2-dimethyl-1,3-dioxalan-4-yl]-4-heptene-1,2-diol 在 sodium periodate 、 正丁基锂 、 4-甲基苯磺酸吡啶 、 sodium hydride 、 四丁基高碘酸铵 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 水 、 苯 为溶剂， 反应 3.58h， 生成 methyl (2E,4S,6Z)-12-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-9-hydroxydodeca-2,6-dien-10-ynoate
  参考文献：
  名称：

  Stereoselective synthesis of syn-2,7-disubstituted-4,5-oxepenes

  摘要：

  An efficient synthesis of the title compounds as pure enantiomers is reported. The method is based on the intramolecular trapping group of a carbocation generated by acid treatment of exo-Co-2(CO)(6)-propargyl alcohols by a stereochemically controlled secondary hydroxy a up located in a suitable chain. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00046-7
• 作为产物：
  描述：

  (S)-7-(tert-Butyl-dimethyl-silanyloxy)-7-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hept-4-yne-1,2-diol 在 Lindlar's catalyst 喹啉 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 反应 0.5h， 以100%的产率得到(2RS,7S)-7-(tert-butyldimethyl-silanyloxy)-7-[(4R)-2,2-dimethyl-1,3-dioxalan-4-yl]-4-heptene-1,2-diol
  参考文献：
  名称：

  Stereoselective synthesis of syn-2,7-disubstituted-4,5-oxepenes

  摘要：

  An efficient synthesis of the title compounds as pure enantiomers is reported. The method is based on the intramolecular trapping group of a carbocation generated by acid treatment of exo-Co-2(CO)(6)-propargyl alcohols by a stereochemically controlled secondary hydroxy a up located in a suitable chain. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00046-7

文献信息

• Stereoselective synthesis of syn-2,7-disubstituted-4,5-oxepenes
  作者：David D Dı́az、Juan M Betancort、Fernando R.P Crisóstomo、Tomás Martı́n、Vı́ctor S Martı́n

  DOI：10.1016/s0040-4020(02)00046-7

  日期：2002.3

  An efficient synthesis of the title compounds as pure enantiomers is reported. The method is based on the intramolecular trapping group of a carbocation generated by acid treatment of exo-Co-2(CO)(6)-propargyl alcohols by a stereochemically controlled secondary hydroxy a up located in a suitable chain. (C) 2002 Elsevier Science Ltd. All rights reserved.