(5S,6R,9R)-6-[(E)-7-[tert-butyl(dimethyl)silyl]oxyhept-1-enyl]-8-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-(methoxymethoxy)-9-methyl-3-phenylmethoxy-1-oxaspiro[4.5]deca-3,7-dien-2-one | 144446-45-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: (5S,6R,9R)-6-[(E)-7-[tert-butyl(dimethyl)silyl]oxyhept-1-enyl]-8-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-(methoxymethoxy)-9-methyl-3-phenylmethoxy-1-oxaspiro[4.5]deca-3,7-dien-2-one
• CAS: 144446-45-7
• 化学式: C₄₉H₆₈O₇Si₂
• 分子量: 825.246
• InChiKey: SVNCHQMLPYSMLG-PFVDQAERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.63
• 重原子数：
  58
• 可旋转键数：
  21
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  methyl (1S,2R,5R)-2-[(E)-7-[tert-butyl(dimethyl)silyl]oxyhept-1-enyl]-4-[[tert-butyl(diphenyl)silyl]oxymethyl]-1-hydroxy-5-methylcyclohex-3-ene-1-carboxylate 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 、 lithium hexamethyldisilazane 作用下， 以 二氯甲烷 为溶剂， 生成 (5S,6R,9R)-6-[(E)-7-[tert-butyl(dimethyl)silyl]oxyhept-1-enyl]-8-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-(methoxymethoxy)-9-methyl-3-phenylmethoxy-1-oxaspiro[4.5]deca-3,7-dien-2-one
  参考文献：
  名称：

  对映选择性合成氯环内酯的上半部分

  摘要：

  描述了对应于氯环硫内酯上半部分的螺酮酸酯4和5的高度对映体和非对映体选择性合成。

  DOI：

  10.1016/s0040-4039(00)61260-1

文献信息

• Enantioselective synthesis of the top half of chlorothricolide
  作者：William R. Roush、Richard J. Sciotti

  DOI：10.1016/s0040-4039(00)61260-1

  日期：1992.8

  Highly enantio- and diastereoselective syntheses of spirotetronates 4 and 5 corresponding to the top half of chlorothricolide are described.

  描述了对应于氯环硫内酯上半部分的螺酮酸酯4和5的高度对映体和非对映体选择性合成。
• Studies on the Synthesis of Chlorothricolide:  Diastereo- and Enantioselective Syntheses of Model Top-Half Spirotetronate Units
  作者：William R. Roush、Richard J. Sciotti

  DOI：10.1021/jo980379w

  日期：1998.8.1

  Highly enantio- and diastereoselective syntheses of spirotetronates 9 and 10, corresponding to the top-half fragment of chlorothricolide, are described. Key steps in these syntheses are the Diels-Alder reactions of trienes 11 and 12 with the chiral dienophile (R)-6 that provide cycloadducts 18 and 38 with remarkably high stereoselectivity. These reactions exhibit exquisite regioselectivity for addition across the trisubstituted C(18)-C(21) diene unit; they also proceed with remarkable orientational control of the dienophile with respect to the C(18)-C(21) diene, as well as with excellent exo diastereofacial selectivity on the part of the chiral dienophile, (R)-6. Results are presented indicating that it is not necessary to control the stereochemistry of the C(20)-C(21) trisubstituted olefin of the triene precursors, as this unit :readily isomerizes under the conditions of the Diels-Alder reaction. Remarkably, the seemingly unreactive (E,E,E)-triene isomers (E,E,E)-11 and (E,E,E)-12 can be used as the starting material for the Diels-Alder reactions, and the desired exo-cycloadducts 18 and 38 are still obtained in good yield, without products of competitive Diels-Alder reactions of the disubstituted C(16)-C(19) dienes being observed.