[(1'R,4S,4aS,5R,7S)-1-[tert-butyl(dimethyl)silyl]oxy-5-(methoxymethoxy)-2',2'-dimethyl-7-prop-2-enylspiro[3,4a,5,6,7,8-hexahydroisochromene-4,6'-cyclohexane]-1'-yl]methoxy-tert-butyl-dimethylsilane | 1448616-46-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: [(1'R,4S,4aS,5R,7S)-1-[tert-butyl(dimethyl)silyl]oxy-5-(methoxymethoxy)-2',2'-dimethyl-7-prop-2-enylspiro[3,4a,5,6,7,8-hexahydroisochromene-4,6'-cyclohexane]-1'-yl]methoxy-tert-butyl-dimethylsilane
• CAS: 1448616-46-3
• 化学式: C₃₄H₆₄O₅Si₂
• 分子量: 609.05
• InChiKey: RWECUKJTJXYIEA-SWPDKZNJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.68
• 重原子数：
  41
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(1'R,4S,4aS,5R,7S)-1-[tert-butyl(dimethyl)silyl]oxy-5-(methoxymethoxy)-2',2'-dimethyl-7-prop-2-enylspiro[3,4a,5,6,7,8-hexahydroisochromene-4,6'-cyclohexane]-1'-yl]methoxy-tert-butyl-dimethylsilane 在 silver tetrafluoroborate 、 氧气 、 乙酸酐 、 臭氧 、 palladium dichloride 作用下， 以 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.67h， 生成 (1S,2R,4a'S,5'R,7'S,9a'S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5'-(methoxymethoxy)-3,3-dimethyl-8'-methylenetetrahydro-1'H,3'H-spiro[cyclohexane-1,4'-[7,9a]methanocyclohepta[c]pyran]-1',9'(4a'H)-dione
  参考文献：
  名称：

  A unified strategy for the synthesis of (−)-maoecrystal Z, (−)-trichorabdal A, and (−)-longikaurin E

  摘要：

  DOI：

  10.1016/j.tet.2014.03.071
• 作为产物：
  描述：

  (2'R,4S,4aR,5R,7S,8aR)-2'-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-hydroxy-3',3'-dimethyl-7-prop-2-enylspiro[4a,5,6,7,8,8a-hexahydro-3H-isochromene-4,1'-cyclohexane]-1-one 在 四丁基碘化铵 、 双(三甲基硅烷基)氨基钾 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.58h， 生成 [(1'R,4S,4aS,5R,7S)-1-[tert-butyl(dimethyl)silyl]oxy-5-(methoxymethoxy)-2',2'-dimethyl-7-prop-2-enylspiro[3,4a,5,6,7,8-hexahydroisochromene-4,6'-cyclohexane]-1'-yl]methoxy-tert-butyl-dimethylsilane
  参考文献：
  名称：

  A Unified Strategy to ent-Kauranoid Natural Products: Total Syntheses of (−)-Trichorabdal A and (−)-Longikaurin E

  摘要：

  The first total syntheses of (-)-trichorabdal A and (-)-longikaurin E are reported. A unified synthetic strategy is employed that relies on a Pd-mediated oxidative cyclization of a silyl ketene acetal to generate an all-carbon quaternary center and build the bicyclo[3.2.1]octane framework. These studies, taken together with our previous synthesis of (-)-maoecrystal Z, demonstrate that three architecturally distinct ent-kauranoids can be prepared from a common spirolactone intermediate.

  DOI：

  10.1021/ja406599a

文献信息

• A Unified Strategy to <i>ent</i>-Kauranoid Natural Products: Total Syntheses of (−)-Trichorabdal A and (−)-Longikaurin E
  作者：John T. S. Yeoman、Victor W. Mak、Sarah E. Reisman

  DOI：10.1021/ja406599a

  日期：2013.8.14

  The first total syntheses of (-)-trichorabdal A and (-)-longikaurin E are reported. A unified synthetic strategy is employed that relies on a Pd-mediated oxidative cyclization of a silyl ketene acetal to generate an all-carbon quaternary center and build the bicyclo[3.2.1]octane framework. These studies, taken together with our previous synthesis of (-)-maoecrystal Z, demonstrate that three architecturally distinct ent-kauranoids can be prepared from a common spirolactone intermediate.
• A unified strategy for the synthesis of (−)-maoecrystal Z, (−)-trichorabdal A, and (−)-longikaurin E
  作者：John T.S. Yeoman、Jacob Y. Cha、Victor W. Mak、Sarah E. Reisman

  DOI：10.1016/j.tet.2014.03.071

  日期：2014.7