<2R-<2α,3α,4α(4R*,6S*),4aα,8β>>-4-<2-<6-<2-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-2-(dimethylphenylsilyl)hexahydro-3-methyl-8-<(trimethylsilyl)oxy>-3H-naphth<1,8a-b>oxiren-5(6H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: <2R-<2α,3α,4α(4R*,6S*),4aα,8β>>-4-<2-<6-<2-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-2-(dimethylphenylsilyl)hexahydro-3-methyl-8-<(trimethylsilyl)oxy>-3H-naphth<1,8a-b>oxiren-5(6H)-one
• 英文别名: (2R,3R,4R,4aR,8R)-4-[2-[(4R,6S)-6-[2-[tert-butyl(diphenyl)silyl]oxyethyl]-2,2-dimethyl-1,3-dioxan-4-yl]ethyl]-2-[dimethyl(phenyl)silyl]-3-methyl-8-trimethylsilyloxy-1a,2,3,4,4a,6,7,8-octahydronaphtho[4a,5-b]oxiren-5-one
• 化学式: C₄₈H₇₀O₆Si₃
• 分子量: 827.337
• InChiKey: BTZGBESTVWLEPL-XWKFHDAESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.23
• 重原子数：
  57
• 可旋转键数：
  14
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  66.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  <2R-<2α,3α,4α(4R*,6S*),4aα,8β>>-4-<2-<6-<2-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-2-(dimethylphenylsilyl)hexahydro-3-methyl-8-<(trimethylsilyl)oxy>-3H-naphth<1,8a-b>oxiren-5(6H)-one 在 sodium periodate 、 四丁基氟化铵 、 4-甲基苯磺酸吡啶 、 溶剂黄146 、 三乙胺 、 间氯过氧苯甲酸 、 lithium diisopropyl amide 作用下， 以 甲醇 为溶剂， 反应 44.42h， 生成 <4R-<4α,5α(4R*,6S*)>>-5-<2-<6-<2-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-4-methyl-2-cyclohexen-1-one
  参考文献：
  名称：

  Studies on the Degradation of Mevinolin and Compactin: A Formal Route to Semisynthetic Analogs

  摘要：

  Procedures are described for degrading mevinolin (1a) and compactin (1b) into the enone 2, which is a substance that has been elaborated into 1a, 1b, and 3-ethylcompactin (1c). Consequently, 2 serves as an advanced intermediate for the construction of semisynthetic analogues of the mevinic acids. The degradation is based largely on a series of oxidations (epoxidation of allylic and homoallylic double bonds, alpha-hydroxylation of a ketone unit) and on S(N)2' addition of phenyldimethylsilyl cuprates to a vinyl epoxide system). These reactions are applied in a way that leads to 33 and 50, which are then cleaved with Pb(OAc)(4) or NaIO4, respectively.

  DOI：

  10.1021/jo00110a051
• 作为产物：
  描述：

  美伐他汀 在 咪唑 、 叔丁基过氧化氢 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 四丙基高钌酸铵 、 bis(acetylacetonate)oxovanadium 、 4 A molecular sieve 、 4-甲基苯磺酸吡啶 、 lithium 、 碳酸氢钠 、 N-甲基吗啉氧化物 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 28.34h， 生成 <2R-<2α,3α,4α(4R*,6S*),4aα,8β>>-4-<2-<6-<2-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-2-(dimethylphenylsilyl)hexahydro-3-methyl-8-<(trimethylsilyl)oxy>-3H-naphth<1,8a-b>oxiren-5(6H)-one
  参考文献：
  名称：

  Studies on the Degradation of Mevinolin and Compactin: A Formal Route to Semisynthetic Analogs

  摘要：

  Procedures are described for degrading mevinolin (1a) and compactin (1b) into the enone 2, which is a substance that has been elaborated into 1a, 1b, and 3-ethylcompactin (1c). Consequently, 2 serves as an advanced intermediate for the construction of semisynthetic analogues of the mevinic acids. The degradation is based largely on a series of oxidations (epoxidation of allylic and homoallylic double bonds, alpha-hydroxylation of a ketone unit) and on S(N)2' addition of phenyldimethylsilyl cuprates to a vinyl epoxide system). These reactions are applied in a way that leads to 33 and 50, which are then cleaved with Pb(OAc)(4) or NaIO4, respectively.

  DOI：

  10.1021/jo00110a051

文献信息

• Studies on the Degradation of Mevinolin and Compactin: A Formal Route to Semisynthetic Analogs
  作者：D. L. J. Clive、Chengzhi Zhang

  DOI：10.1021/jo00110a051

  日期：1995.3

  Procedures are described for degrading mevinolin (1a) and compactin (1b) into the enone 2, which is a substance that has been elaborated into 1a, 1b, and 3-ethylcompactin (1c). Consequently, 2 serves as an advanced intermediate for the construction of semisynthetic analogues of the mevinic acids. The degradation is based largely on a series of oxidations (epoxidation of allylic and homoallylic double bonds, alpha-hydroxylation of a ketone unit) and on S(N)2' addition of phenyldimethylsilyl cuprates to a vinyl epoxide system). These reactions are applied in a way that leads to 33 and 50, which are then cleaved with Pb(OAc)(4) or NaIO4, respectively.