6(R)-<2-<8(S)-<(2,2-dimethylbutyryl)oxy>-2(S),6(R)-dimethyl-1,2,3,4,6,7,8,8a(R)-octahydronaphthyl-1(S)>ethyl>-4(R)-<(tert-butyldimethylsilyl)oxy>-3,4,5,6-tetrahydro-2H-pyran-2-one | 127343-13-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 6(R)-<2-<8(S)-<(2,2-dimethylbutyryl)oxy>-2(S),6(R)-dimethyl-1,2,3,4,6,7,8,8a(R)-octahydronaphthyl-1(S)>ethyl>-4(R)-<(tert-butyldimethylsilyl)oxy>-3,4,5,6-tetrahydro-2H-pyran-2-one
• 英文别名: 6(R)-[2-[8(S)-(2,2-dimethylbutyryloxy)-2(S)-methyl-6(R)-methyl-1,2,3,4, 6,7,8,8a(R)-octahydronaphthyl-1(S)]ethyl]-4(R)-tertbutyldimethylsilyloxy-3,4,5,6-tetrahydro-2H-pyran-2-one；[(1S,3R,7S,8S,8aR)-8-[2-[(2R,4R)-4-[tert-butyl(dimethyl)silyl]oxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,5,6,7,8,8a-octahydronaphthalen-1-yl] 2,2-dimethylbutanoate
• CAS: 127343-13-9
• 化学式: C₃₁H₅₄O₅Si
• 分子量: 534.852
• InChiKey: VJCQTYIUHFNKOR-ZNFHGHDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.84
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6(R)-<2-<8(S)-<(2,2-dimethylbutyryl)oxy>-2(S),6(R)-dimethyl-1,2,3,4,6,7,8,8a(R)-octahydronaphthyl-1(S)>ethyl>-4(R)-<(tert-butyldimethylsilyl)oxy>-3,4,5,6-tetrahydro-2H-pyran-2-one 生成 [(1S,3R,4S,4aS,7S,8S,8aS)-4a-bromo-8-[2-[(2R,4R)-4-[tert-butyl(dimethyl)silyl]oxy-6-oxooxan-2-yl]ethyl]-4-hydroxy-3,7-dimethyl-2,3,4,5,6,7,8,8a-octahydro-1H-naphthalen-1-yl] 2,2-dimethylbutanoate
  参考文献：
  名称：

  DUGGAN, MARK E.

  摘要：

  DOI：
• 作为产物：
  描述：

  辛伐他汀 在 Wilkinson's catalyst 咪唑 、 氢气 、 硫脲 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 44.0h， 生成 6(R)-<2-<8(S)-<(2,2-dimethylbutyryl)oxy>-2(S),6(R)-dimethyl-1,2,3,4,6,7,8,8a(R)-octahydronaphthyl-1(S)>ethyl>-4(R)-<(tert-butyldimethylsilyl)oxy>-3,4,5,6-tetrahydro-2H-pyran-2-one
  参考文献：
  名称：

  3-羟基-3-甲基戊二酰辅酶a还原酶抑制剂。7.辛伐他汀的六氢萘部分的修饰：5-氧化的和5-氧杂的衍生物。

  摘要：

  通过氧合和氧杂取代对辛伐他汀2a中的六氢萘环5位进行修饰，得到了两个衍生物系列，分别在体外评估了对3-羟基-3-甲基戊二酰辅酶A还原酶的抑制作用，并在体内急性评估了其作为α-羟色胺抑制剂的口服效果大鼠的胆固醇生成。在选择用于进一步生物学评估的化合物中，3,4,4a，5-四氢2a的6个β-甲基-5-氧杂10和5个α-羟基16衍生物，以及16个的6个β-表观异构体14证明在胆甾醇胺引发的狗中作为降胆固醇药具有口服活性。随后在狗中进行的急性口腔新陈代谢研究表明，化合物14和16的峰值血浆药物活性和曲线下面积值比化合物10低，并导致选择14和16进行毒理学评估。

  DOI：

  10.1021/jm00112a027

文献信息

• Novel synthesis of mevinolin-related compounds. Large-scale preparation of HMG-CoA reductase inhibitor L-679,336
  作者：Ann E. DeCamp、Sander G. Mills、Alan T. Kawaguchi、Richard Desmond、Robert A. Reamer、Lisa DiMichele、R. P. Volante

  DOI：10.1021/jo00011a022

  日期：1991.5

  A novel synthetic route to a mevinolin-related HMG-CoA reductase inhibitor L-679,336 is described. The key features of the synthesis are a diastereoselective osmium tetraoxide catalyzed dihydroxylation reaction and a highly selective, phosphorus-mediated, pinacol-type rearrangement to give ketone 6. In situ multinuclear NMR experiments were used to gain a detailed understanding of the pinacol step. The above route was used for multikilogram preparation of the title compound. Also described are Lewis acid catalyzed rearrangement reactions of epoxide intermediates 4 and 5, as well as the intramolecular hydrosilylation reaction of deacylated olefinic substrates 17 and 18.
• CAMP, ANN E. DE;MILLS, SANDER G.;KAWAGUCHI, ALAN T.;DESMOND, RICHARD;REAM+, J. ORG. CHEM., 56,(1991) N1, C. 3564-3571
  作者：CAMP, ANN E. DE、MILLS, SANDER G.、KAWAGUCHI, ALAN T.、DESMOND, RICHARD、REAM+

  DOI：——

  日期：——
• DUGGAN, MARK E.;ALBERTS, ALFRED W.;BOSTEDOR, RICK;CHAO, YU-SHENG;GERMERSH+, J. MED. CHEM., 34,(1991) N, C. 2489-2495
  作者：DUGGAN, MARK E.、ALBERTS, ALFRED W.、BOSTEDOR, RICK、CHAO, YU-SHENG、GERMERSH+

  DOI：——

  日期：——