6(R)-<2-<8(S)-<(2,2-dimethylbutyryl)oxy>-4a(R),5(S)-dihydroxy-2(S),6(R)-dimethyl-1,2,3,4,4a,5,6,7,8,8a(R)-decahydronaphth-1(S)-yl>ethyl>-4(R)-(tert-butyldimethylsiloxy)-3,4,5,6-tetrahydro-2H-pyran-2-one | 134004-76-5

• 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>-4a(R),5(S)-dihydroxy-2(S),6(R)-dimethyl-1,2,3,4,4a,5,6,7,8,8a(R)-decahydronaphth-1(S)-yl>ethyl>-4(R)-(tert-butyldimethylsiloxy)-3,4,5,6-tetrahydro-2H-pyran-2-one
• 英文别名: [(1S,3R,4S,4aR,7S,8S,8aS)-8-[2-[(2R,4R)-4-[tert-butyl(dimethyl)silyl]oxy-6-oxooxan-2-yl]ethyl]-4,4a-dihydroxy-3,7-dimethyl-2,3,4,5,6,7,8,8a-octahydro-1H-naphthalen-1-yl] 2,2-dimethylbutanoate
• CAS: 134004-76-5
• 化学式: C₃₁H₅₆O₇Si
• 分子量: 568.867
• InChiKey: ZGPCWUKTXCEJGX-SRXHVFICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.0
• 重原子数：
  39.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  102.29
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  6(R)-<2-<8(S)-<(2,2-dimethylbutyryl)oxy>-4a(R),5(S)-dihydroxy-2(S),6(R)-dimethyl-1,2,3,4,4a,5,6,7,8,8a(R)-decahydronaphth-1(S)-yl>ethyl>-4(R)-(tert-butyldimethylsiloxy)-3,4,5,6-tetrahydro-2H-pyran-2-one 在 水 、 N,N-二异丙基乙胺 作用下， 以 氘代乙腈 为溶剂， 反应 19.5h， 生成 2,2-Dimethyl-butyric acid (1S,3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-4-hydroxy-3,7-dimethyl-1,2,3,5,6,7,8,8a-octahydro-naphthalen-1-yl ester
  参考文献：
  名称：

  Novel synthesis of mevinolin-related compounds. Large-scale preparation of HMG-CoA reductase inhibitor L-679,336

  摘要：

  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.

  DOI：

  10.1021/jo00011a022
• 作为产物：
  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 、 四氧化锇 生成 6(R)-<2-<8(S)-<(2,2-dimethylbutyryl)oxy>-4a(R),5(S)-dihydroxy-2(S),6(R)-dimethyl-1,2,3,4,4a,5,6,7,8,8a(R)-decahydronaphth-1(S)-yl>ethyl>-4(R)-(tert-butyldimethylsiloxy)-3,4,5,6-tetrahydro-2H-pyran-2-one
  参考文献：
  名称：

  CAMP, ANN E. DE;MILLS, SANDER G.;KAWAGUCHI, ALAN T.;DESMOND, RICHARD;REAM+, J. ORG. CHEM., 56,(1991) N1, C. 3564-3571

  摘要：

  DOI：