4(R)-(tert-butyldimethylsiloxy)-6(R)-<2-<8(S)-<(4-fluorobenzyl)oxy>-1,2,6,7,8,8a(S)-hexahydro-2(S),6(R)-dimethyl-1(S)-naphthyl>ethyl>-3,4,5,6-tetrahydro-2H-pyran-2-one | 79691-21-7

• 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: 4(R)-(tert-butyldimethylsiloxy)-6(R)-<2-<8(S)-<(4-fluorobenzyl)oxy>-1,2,6,7,8,8a(S)-hexahydro-2(S),6(R)-dimethyl-1(S)-naphthyl>ethyl>-3,4,5,6-tetrahydro-2H-pyran-2-one
• 英文别名: (4R,6R)-6-[2-[(1S,2S,6R,8S,8aR)-8-[(4-fluorophenyl)methoxy]-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]ethyl]-4-[tert-butyl(dimethyl)silyl]oxyoxan-2-one
• CAS: 79691-21-7
• 化学式: C₃₂H₄₇FO₄Si
• 分子量: 542.807
• InChiKey: UJQBJKCWKONAEZ-MDGVESEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.99
• 重原子数：
  38.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4(R)-(tert-butyldimethylsiloxy)-6(R)-<2-<8(S)-<(4-fluorobenzyl)oxy>-1,2,6,7,8,8a(S)-hexahydro-2(S),6(R)-dimethyl-1(S)-naphthyl>ethyl>-3,4,5,6-tetrahydro-2H-pyran-2-one 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以99%的产率得到6(R)-<2-<8(S)-<(4-fluorobenzyl)oxy>-1,2,6,7,8,8a(S)-hexahydro-2(S),6(R)-dimethyl-1(S)-naphthyl>ethyl>-4(R)-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one
  参考文献：
  名称：

  3-Hydroxy-3-methylglutaryl-coenzyme A reductase inhibitors. 8. Side chain ether analogs of lovastatin

  摘要：

  A general route for preparing side chain ether analogues of lovastatin is presented. These analogues proved to be weaker inhibitors of HMG-CoA reductase than the corresponding side chain ester analogues. Interestingly, inhibitory potency was enhanced markedly when the 4-fluoro group was incorporated in the aromatic moiety of the side chain benzyl group of 2d.

  DOI：

  10.1021/jm00112a024
• 作为产物：
  描述：

  4-氟氯苄 在 吡啶 、 chromium(VI) oxide 、 水 、 4-甲基苯磺酸吡啶 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 83.01h， 生成 4(R)-(tert-butyldimethylsiloxy)-6(R)-<2-<8(S)-<(4-fluorobenzyl)oxy>-1,2,6,7,8,8a(S)-hexahydro-2(S),6(R)-dimethyl-1(S)-naphthyl>ethyl>-3,4,5,6-tetrahydro-2H-pyran-2-one
  参考文献：
  名称：

  3-Hydroxy-3-methylglutaryl-coenzyme A reductase inhibitors. 8. Side chain ether analogs of lovastatin

  摘要：

  A general route for preparing side chain ether analogues of lovastatin is presented. These analogues proved to be weaker inhibitors of HMG-CoA reductase than the corresponding side chain ester analogues. Interestingly, inhibitory potency was enhanced markedly when the 4-fluoro group was incorporated in the aromatic moiety of the side chain benzyl group of 2d.

  DOI：

  10.1021/jm00112a024

文献信息

• DECAMP, ANN E.;VERHOEVEN, THOMAS R.;SHINKAI, ICHIRO
  作者：DECAMP, ANN E.、VERHOEVEN, THOMAS R.、SHINKAI, ICHIRO

  DOI：——

  日期：——
• LEE, T. -J.;HOLTZ, W. J.;SMITH, R. L.;ALBERTS, A. W.;GILFILLAN, J. L., J. MED. CHEM., 34,(1991) N, C. 2474-2477
  作者：LEE, T. -J.、HOLTZ, W. J.、SMITH, R. L.、ALBERTS, A. W.、GILFILLAN, J. L.

  DOI：——

  日期：——