<1R-<1α,2α,4α,4aβ,5β(4R*,6S*),6β,7β>>-5-<2-<6-<2-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-7-(dimethylphenylsilyl)-1,2,3,4,4a,5,6,7-octahydro-2,6-dimethyl-1,4-naphthalenediol | 161466-46-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: <1R-<1α,2α,4α,4aβ,5β(4R*,6S*),6β,7β>>-5-<2-<6-<2-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-7-(dimethylphenylsilyl)-1,2,3,4,4a,5,6,7-octahydro-2,6-dimethyl-1,4-naphthalenediol
• CAS: 161466-46-2
• 化学式: C₄₆H₆₆O₅Si₂
• 分子量: 755.198
• InChiKey: KCFGSEZAIZLJCG-QZFSRLPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  53.0
• 可旋转键数：
  11.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  68.15
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  <1R-<1α,2α,4α,4aβ,5β(4R*,6S*),6β,7β>>-5-<2-<6-<2-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-7-(dimethylphenylsilyl)-1,2,3,4,4a,5,6,7-octahydro-2,6-dimethyl-1,4-naphthalenediol 在 叔丁基过氧化氢 、 bis(acetylacetonate)oxovanadium 、 碳酸氢钠 作用下， 以 苯 为溶剂， 反应 3.0h， 以84%的产率得到<2R-<2α,3α,4α(4R*,6S*),4aα,5β,7β,8β>>-4-<2-<6-<2-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-2-(dimethylphenylsilyl)octahydro-3,7-dimethyl-3H-naphth<1,8a-b>oxirene-5,8-diol
  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：

  洛伐他汀 在 咪唑 、 叔丁基过氧化氢 、 lithium aluminium tetrahydride 、 bis(acetylacetonate)oxovanadium 、 lithium 、 碳酸氢钠 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 15.0h， 生成 <1R-<1α,2α,4α,4aβ,5β(4R*,6S*),6β,7β>>-5-<2-<6-<2-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-7-(dimethylphenylsilyl)-1,2,3,4,4a,5,6,7-octahydro-2,6-dimethyl-1,4-naphthalenediol
  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

• Addition of dimethylphenylsilyl cuprates to vinyl epoxides: Effect of cuprate stoichiometry on stereochemistry and refiochemistry
  作者：Derrick L.J. Clive、Chengzhi Zhang、Yuanxi Zhou、Yong Tao

  DOI：10.1016/0022-328x(94)05224-y

  日期：1995.3

  The stereochemical and regiochemical outcome of reactions of PhMe2SiLi/CuCN mixtures with vinyl epoxides depends on the PhMe2SiLi/CuCn ratio.

  PhMe 2 SiLi / CuCN混合物与乙烯基环氧化物反应的立体化学和区域化学结果取决于PhMe 2 SiLi / CuCn比。