(4R,5R,6R,7S)-6-(tert-butyldimethylsilyloxy)-5,7-bis(methoxymethoxy)undec-1-en-4-yl acrylate | 503417-20-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (4R,5R,6R,7S)-6-(tert-butyldimethylsilyloxy)-5,7-bis(methoxymethoxy)undec-1-en-4-yl acrylate
• 英文别名: [(4R,5R,6R,7S)-6-[tert-butyl(dimethyl)silyl]oxy-5,7-bis(methoxymethoxy)undec-1-en-4-yl] prop-2-enoate
• CAS: 503417-20-7
• 化学式: C₂₄H₄₆O₇Si
• 分子量: 474.711
• InChiKey: DWAJVQZKCSPGRF-KKSHJYNMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.22
• 重原子数：
  32
• 可旋转键数：
  20
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (4R,5R,6R,7S)-6-(tert-butyldimethylsilyloxy)-5,7-bis(methoxymethoxy)undec-1-en-4-yl acrylate 在 Grubbs catalyst first generation 、 二甲基硫 、 三氟化硼乙醚 、 氢氟酸 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 5.5h， 生成 6-(1,2,3-trihydroxy-heptyl)-5,6-dihydro-pyran-2-one
  参考文献：
  名称：

  Erythrulose derivatives as functionalized chiral d3 and d4 synthons

  摘要：

  Protected erythrulose derivatives have been shown to undergo highly stereoselective dicyclohexylboron chloride-mediated aldol reactions. After suitable synthetic manipulation of the resulting aldol adducts, chiral polyoxygenated molecules can be obtained in which either three or all four carbon atoms of the starting erythrulose molecule have been incorporated. Erythrulose derivatives may therefore behave, according to convenience, as chiral, functionalized d(3) or d(4) synthons. As an example, this methodology has been applied to a stereoselective synthesis of the naturally occurring, pharmacologically active lactone (+)-boronolide. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00638-9
• 作为产物：
  描述：

  2-[tert-butyl(dimethyl)silyl]oxy-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanone 在 4-二甲氨基吡啶 、 copper(l) iodide 、 锂硼氢 、 氯代二环己基硼烷 、 4-甲基苯磺酸吡啶 、 potassium carbonate 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 108.75h， 生成 (4R,5R,6R,7S)-6-(tert-butyldimethylsilyloxy)-5,7-bis(methoxymethoxy)undec-1-en-4-yl acrylate
  参考文献：
  名称：

  Erythrulose derivatives as functionalized chiral d3 and d4 synthons

  摘要：

  Protected erythrulose derivatives have been shown to undergo highly stereoselective dicyclohexylboron chloride-mediated aldol reactions. After suitable synthetic manipulation of the resulting aldol adducts, chiral polyoxygenated molecules can be obtained in which either three or all four carbon atoms of the starting erythrulose molecule have been incorporated. Erythrulose derivatives may therefore behave, according to convenience, as chiral, functionalized d(3) or d(4) synthons. As an example, this methodology has been applied to a stereoselective synthesis of the naturally occurring, pharmacologically active lactone (+)-boronolide. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00638-9

文献信息

• Erythrulose derivatives as functionalized chiral d3 and d4 synthons
  作者：Juan Murga、Eva Falomir、Miguel Carda、J.Alberto Marco

  DOI：10.1016/s0957-4166(02)00638-9

  日期：2002.10

  Protected erythrulose derivatives have been shown to undergo highly stereoselective dicyclohexylboron chloride-mediated aldol reactions. After suitable synthetic manipulation of the resulting aldol adducts, chiral polyoxygenated molecules can be obtained in which either three or all four carbon atoms of the starting erythrulose molecule have been incorporated. Erythrulose derivatives may therefore behave, according to convenience, as chiral, functionalized d(3) or d(4) synthons. As an example, this methodology has been applied to a stereoselective synthesis of the naturally occurring, pharmacologically active lactone (+)-boronolide. (C) 2002 Elsevier Science Ltd. All rights reserved.