<1aR-<1aα,4β,4aα,5α(4R*,6S*),6α>>-5-<2-<6-<2-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-1a,2,4,4a,5,6-hexahydro-6-methyl-3H-naphth<1,8a-b>oxiren-4-ol | 161466-61-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: <1aR-<1aα,4β,4aα,5α(4R*,6S*),6α>>-5-<2-<6-<2-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-1a,2,4,4a,5,6-hexahydro-6-methyl-3H-naphth<1,8a-b>oxiren-4-ol
• 英文别名: (1aR,4S,4aS,5S,6S,8aS)-5-[2-[(4R,6S)-6-[2-[tert-butyl(diphenyl)silyl]oxyethyl]-2,2-dimethyl-1,3-dioxan-4-yl]ethyl]-6-methyl-2,3,4,4a,5,6-hexahydro-1aH-naphtho[4,4a-b]oxiren-4-ol
• CAS: 161466-61-1
• 化学式: C₃₇H₅₂O₅Si
• 分子量: 604.902
• InChiKey: UEUUOQHZWZFHCQ-LWALBORZSA-N

物化性质

• 沸点：
  647.6±55.0 °C(predicted)
• 密度：
  1.12±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.37
• 重原子数：
  43
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  60.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  <1aR-<1aα,4β,4aα,5α(4R*,6S*),6α>>-5-<2-<6-<2-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-1a,2,4,4a,5,6-hexahydro-6-methyl-3H-naphth<1,8a-b>oxiren-4-ol 在 叔丁基过氧化氢 、 4-二甲氨基吡啶 、 四丙基高钌酸铵 、 bis(acetylacetonate)oxovanadium 、 4 A molecular sieve 、 四丁基氟化铵 、 4-甲基苯磺酸吡啶 、 lithium 、 碳酸氢钠 、 溶剂黄146 、 N-甲基吗啉氧化物 、 三乙胺 、 间氯过氧苯甲酸 、 lithium diisopropyl amide 作用下， 以 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 35.09h， 生成 <4R-<4α,7β,8β(4R*,6S*),8aβ>>-4-<2-<6-<2-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-3,4,4a,7,8,8a-hexahydro-2,4,4a-trihydroxy-7-methyl-1(2H)naphthalenone
  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：

  <1S-<1α(3R*,5S*),2α,8β,8aα>>-1<<(1,1-Dimethylethyl)diphenylsilyl>oxy>-7-(1,2,6,7,8,8a-hexahydro-8-hydroxy-2-methyl-1-naphthalenyl)-3,5-heptanediol 在 叔丁基过氧化氢 、 bis(acetylacetonate)oxovanadium 、 4-甲基苯磺酸吡啶 、 碳酸氢钠 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 2.17h， 生成 <1aR-<1aα,4β,4aα,5α(4R*,6S*),6α>>-5-<2-<6-<2-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-1a,2,4,4a,5,6-hexahydro-6-methyl-3H-naphth<1,8a-b>oxiren-4-ol
  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。