5(S)-<<(tert-Butyldiphenylsilyl)oxy>methyl>-3-<1-<4(S)-<5(R)-ethyl-6(R)-methyl-2(S)-phenyldioxanyl>>methyl>-4(R)-methyldihydro-2(3H)-furanone | 137871-07-9

• 分子结构分类: 有机化合物
• 英文名称: 5(S)-<<(tert-Butyldiphenylsilyl)oxy>methyl>-3-<1-<4(S)-<5(R)-ethyl-6(R)-methyl-2(S)-phenyldioxanyl>>methyl>-4(R)-methyldihydro-2(3H)-furanone
• 英文别名: (4R,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-[[(2S,4R,5R,6R)-5-ethyl-6-methyl-2-phenyl-1,3-dioxan-4-yl]methyl]-4-methyloxolan-2-one
• CAS: 137871-07-9
• 化学式: C₃₆H₄₆O₅Si
• 分子量: 586.844
• InChiKey: YIMHAGYEACZCHL-YDQOHYPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.66
• 重原子数：
  42
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5(S)-<<(tert-Butyldiphenylsilyl)oxy>methyl>-3-<1-<4(S)-<5(R)-ethyl-6(R)-methyl-2(S)-phenyldioxanyl>>methyl>-4(R)-methyldihydro-2(3H)-furanone 在 palladium diacetate 叔丁基过氧化氢 、 二甲基硫 、 二异丁基氢化铝 、 碳酸氢钠 、 臭氧 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 、 苯 为溶剂， 反应 12.67h， 生成 4(S)-(Benzoyloxy)-2-<3-<(tert-butyldiphenylsilyl)oxy>-2(S)-(formyloxy)-1(S)-methylpropyl>-5(R)-ethyl-2(R)-hydroxy-6(R)-methyltetrahydro-2H-pyran
  参考文献：
  名称：

  Synthetic studies on the macrodiolide elaiophylin

  摘要：

  An approach to the synthesis of the monomeric fragment of the macrodiolide elaiophylin is reported. The absolute stereochemistry of C5-C-10 is contained in fragment 5 and that of C-13-C-15 is incorporated in aldehyde 6b. A method for the union of these fragments is outlined.

  DOI：

  10.1021/jo00023a017
• 作为产物：
  描述：

  (Z)-5(S)-<<(tert-Butyldiphenylsilyl)oxy>methyl>-3-<<4(S)-<5(R)-ethyl-6(R)-methyl-2(S)-phenyldioxanyl>>methylene>-4(R)-methyldihydro-2(3H)-furanone 在 copper(l) iodide 、 红铝 、 仲丁醇 作用下， 以 四氢呋喃 为溶剂， 以29.06 mg的产率得到5(S)-<<(tert-Butyldiphenylsilyl)oxy>methyl>-3-<1-<4(S)-<5(R)-ethyl-6(R)-methyl-2(S)-phenyldioxanyl>>methyl>-4(R)-methyldihydro-2(3H)-furanone
  参考文献：
  名称：

  Synthetic studies on the macrodiolide elaiophylin

  摘要：

  An approach to the synthesis of the monomeric fragment of the macrodiolide elaiophylin is reported. The absolute stereochemistry of C5-C-10 is contained in fragment 5 and that of C-13-C-15 is incorporated in aldehyde 6b. A method for the union of these fragments is outlined.

  DOI：

  10.1021/jo00023a017