<1S-<1α,7β,8β(4S*,6R*),8aβ>>-8-<2-<6-<2-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-1,2,6,7,8,8a-hexahydro-7-methyl-1-naphthalenol | 117065-48-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: <1S-<1α,7β,8β(4S*,6R*),8aβ>>-8-<2-<6-<2-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-1,2,6,7,8,8a-hexahydro-7-methyl-1-naphthalenol
• 英文别名: (1S,7S,8S,8aR)-8-[2-[(4R,6S)-6-[2-[tert-butyl(diphenyl)silyl]oxyethyl]-2,2-dimethyl-1,3-dioxan-4-yl]ethyl]-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-ol
• CAS: 117065-48-2
• 化学式: C₃₇H₅₂O₄Si
• 分子量: 588.903
• InChiKey: UKVDKPVJAIPYOQ-IBMBEEBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.16
• 重原子数：
  42
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  <1S-<1α,7β,8β(4S*,6R*),8aβ>>-8-<2-<6-<2-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-1,2,6,7,8,8a-hexahydro-7-methyl-1-naphthalenol 在 盐酸 、 4-二甲氨基吡啶 、 草酰氯 、 Celite 、 四丁基氟化铵 、 二甲基亚砜 、 三乙胺 、 silver carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 74.08h， 生成 美伐他汀
  参考文献：
  名称：

  (+)-compactin 和 (+)-mevinolin 的全合成。基于使用特殊钛试剂进行二羰基偶联的一般策略

  摘要：

  描述了一种用于立体控制合成低胆固醇化合物 (+)-compactin(+)-mevinolin 的策略

  DOI：

  10.1021/ja00164a024
• 作为产物：
  描述：

  美伐他汀 在 咪唑 、 lithium aluminium tetrahydride 、 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.17h， 生成 <1S-<1α,7β,8β(4S*,6R*),8aβ>>-8-<2-<6-<2-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-1,2,6,7,8,8a-hexahydro-7-methyl-1-naphthalenol
  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

• Total synthesis of both (+)-compactin and (+)-mevinolin. A general strategy based on the use of a special TiCl3/C8K mixture for dicarbonyl coupling
  作者：Derrick L. J. Clive、K. S. Keshava. Murthy、Andrew G. H. Wee、J. Siva. Prasad、Gil V. J. Da Silva、Marek. Majewski、Paul C. Anderson、Richard D. Haugen、Louis D. Heerze

  DOI：10.1021/ja00228a067

  日期：1988.9
• Total synthesis of both (+)-compactin and (+)-mevinolin. A general strategy based on the use of a special titanium reagent for dicarbonyl coupling
  作者：Derrick L. J. Clive、K. S. Keshava Murthy、Andrew G. H. Wee、J. Siva Prasad、Gil V. J. Da Silva、Marek Majewski、Paul C. Anderson、Claire F. Evans、Richard D. Haugen

  DOI：10.1021/ja00164a024

  日期：1990.4

  A strategy is described for stereocontrolled synthesis of hypocholesterolemic compounds, (+)-compactin(+)-mevinolin

  描述了一种用于立体控制合成低胆固醇化合物 (+)-compactin(+)-mevinolin 的策略
• 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.