methyl (1R,2Z,5S,6S)-6-[2-[(4R,6S)-6-[2-[tert-butyl(diphenyl)silyl]oxyethyl]-2,2-dimethyl-1,3-dioxan-4-yl]ethyl]-5-methyl-2-[(2S)-2-methyl-3-oxopropylidene]cyclohex-3-ene-1-carboxylate | 1026249-35-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (1R,2Z,5S,6S)-6-[2-[(4R,6S)-6-[2-[tert-butyl(diphenyl)silyl]oxyethyl]-2,2-dimethyl-1,3-dioxan-4-yl]ethyl]-5-methyl-2-[(2S)-2-methyl-3-oxopropylidene]cyclohex-3-ene-1-carboxylate
• CAS: 1026249-35-3
• 化学式: C₃₉H₅₄O₆Si
• 分子量: 646.94
• InChiKey: BMSNDESHDQBRJM-YTVYQBFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.02
• 重原子数：
  46
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (1R,2Z,5S,6S)-6-[2-[(4R,6S)-6-[2-[tert-butyl(diphenyl)silyl]oxyethyl]-2,2-dimethyl-1,3-dioxan-4-yl]ethyl]-5-methyl-2-[(2S)-2-methyl-3-oxopropylidene]cyclohex-3-ene-1-carboxylate 在 sodium tetrahydroborate 作用下， 生成 methyl (1R,2Z,5S,6S)-6-[2-[(4R,6S)-6-[2-[tert-butyl(diphenyl)silyl]oxyethyl]-2,2-dimethyl-1,3-dioxan-4-yl]ethyl]-2-[(2S)-3-hydroxy-2-methylpropylidene]-5-methylcyclohex-3-ene-1-carboxylate
  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 、 lead(IV) acetate 、 lithium aluminium tetrahydride 、 正丁基锂 、 碳酸氢钠 、 对甲苯磺酸 、 间氯过氧苯甲酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 5.0h， 生成 methyl (1R,2Z,5S,6S)-6-[2-[(4R,6S)-6-[2-[tert-butyl(diphenyl)silyl]oxyethyl]-2,2-dimethyl-1,3-dioxan-4-yl]ethyl]-5-methyl-2-[(2S)-2-methyl-3-oxopropylidene]cyclohex-3-ene-1-carboxylate
  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.