<1S-<1α(3R*,5S*),2α,6β,8β,8aα>>-7-(1,2,6,7,8,8a-Hexahydro-8-hydroxy-2,6-dimethyl-1-naphthalenyl)-1,3,5-heptanetriol | 148969-22-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: <1S-<1α(3R*,5S*),2α,6β,8β,8aα>>-7-(1,2,6,7,8,8a-Hexahydro-8-hydroxy-2,6-dimethyl-1-naphthalenyl)-1,3,5-heptanetriol
• 英文别名: (3S,5R)-7-[(1S,2S,6R,8S,8aR)-8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]heptane-1,3,5-triol
• CAS: 148969-22-6
• 化学式: C₁₉H₃₂O₄
• 分子量: 324.461
• InChiKey: JFKYPEXUHQECAG-VXCUADNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  洛伐他汀	lovastatin	75330-75-5	C24H36O5	404.547

反应信息

• 作为反应物：
  描述：

  <1S-<1α(3R*,5S*),2α,6β,8β,8aα>>-7-(1,2,6,7,8,8a-Hexahydro-8-hydroxy-2,6-dimethyl-1-naphthalenyl)-1,3,5-heptanetriol 在 咪唑 、 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 为溶剂， 生成 (2S,3S,7S,8S,8aR)-8-[2-[(4R,6S)-6-[2-[tert-butyl(diphenyl)silyl]oxyethyl]-2,2-dimethyl-1,3-dioxan-4-yl]ethyl]-2-hydroxy-3,7-dimethyl-3,7,8,8a-tetrahydro-2H-naphthalen-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：

  洛伐他汀 在 lithium aluminium tetrahydride 作用下， 以84%的产率得到<1S-<1α(3R*,5S*),2α,6β,8β,8aα>>-7-(1,2,6,7,8,8a-Hexahydro-8-hydroxy-2,6-dimethyl-1-naphthalenyl)-1,3,5-heptanetriol
  参考文献：
  名称：

  Formal preparation of semisynthetic analogues of the cholesterol-lowering agent mevinolin

  摘要：

  降胆固醇剂 mevinolin 1 已降解为烯酮 4，而烯酮 4 此前已合成并转化为 mevinolin1、compactin 2 和 3-ethylconipactin3。

  DOI：

  10.1039/c39930000647

文献信息

• Biosynthesis of ML-236C and the hypocholesterolemic agents compactin by Penicillium aurantiogriseum and lovastatin by Aspergillus terreus: determination of the origin of carbon, hydrogen and oxygen atoms by 13C NMR spectrometry and observation of unusual labelling of acetate-derived oxygens by 18O2
  作者：Kurt Wagschal、Yuko Yoshizawa、David J. Witter、Yaoquan Liu、John C. Vederas

  DOI：10.1039/p19960002357

  日期：——

  the hypocholesterolemic agent compactin 3 by cultures of Penicillium aurantiogriseum, and the regiochemical distribution of 2H, 13C and 18O is determined by 13C NMR spectrometry. In addition, sodium [1-13C, 18O2]acetate and 18O2 are incorporated into lovastatin (mevinolin) 4 by cultures of Aspergillus terreus to re-examine the origin of oxygen atoms. The results show that the main-chain oxygen atoms

  钠[1- 13 C，2- 2 ħ 3 ] - ，[2- 13 C，2- 2 ħ 3 ] -和[1- 13 C，18 Ò 2 ] -乙酸甲酯被并入在单独的实验成ML-236C 2和降胆固醇药致密素3的培养分别是aurantiogriseum青霉，并通过13 C NMR光谱法确定2 H，13 C和18 O的区域化学分布。此外，钠[1- 13 C，18 Ò 2〕乙酸甲酯和18 Ò 2通过土曲霉的培养物将它们掺入洛伐他汀（mevinolin）4中，以重新检查氧原子的起源。结果表明，2-4的主链氧原子源自乙酸盐，而3和4的C-8氧原子源自分子氧。但是，详细的质谱分析表明，通常在乙酸氧标记的位点上可以掺入大量需氧，大概是通过脂肪的ω-氧化生成[ 18 O]乙酸盐。根据标记结果，提出了一种机制来解释这些化合物中双环系统的形成。
• 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.
• Formal preparation of semisynthetic analogues of the cholesterol-lowering agent mevinolin
  作者：Derrick L. J. Clive、Chengzhi Zhang

  DOI：10.1039/c39930000647

  日期：——

  The cholesterol-lowering agent mevinolin 1 has been degraded to the enone 4 which had previously been synthesized and converted into mevinolin1, compactin 2 and 3-ethylconipactin3.

  降胆固醇剂 mevinolin 1 已降解为烯酮 4，而烯酮 4 此前已合成并转化为 mevinolin1、compactin 2 和 3-ethylconipactin3。