(1S,3S,7S,8S,8aR)-8-(tert-Butyl-dimethyl-silanyloxymethyl)-3,7-dimethyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-ol | 158041-76-0

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (1S,3S,7S,8S,8aR)-8-(tert-Butyl-dimethyl-silanyloxymethyl)-3,7-dimethyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-ol
• 英文别名: (1S,3S,7S,8S,8aR)-8-[[tert-butyl(dimethyl)silyl]oxymethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-ol
• CAS: 158041-76-0
• 化学式: C₁₉H₃₄O₂Si
• 分子量: 322.563
• InChiKey: ALQYLONQOBQNEP-SRIISGBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.77
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,3S,7S,8S,8aR)-8-(tert-Butyl-dimethyl-silanyloxymethyl)-3,7-dimethyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-ol 在 4-二甲氨基吡啶 、 草酰氯 、 四丁基氟化铵 、 溶剂黄146 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 8.5h， 生成 (S)-2-Methyl-butyric acid (1S,3S,7S,8S,8aR)-8-formyl-3,7-dimethyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester
  参考文献：
  名称：

  Enantioselective Total Synthesis of (+)-6-epi-Mevinolin and Its Analogs. Efficient Construction of the Hexahydronaphthalene Moiety by High Pressure-Promoted Intramolecular Diels−Alder Reaction of (R,2Z,8E,10E)-1-[(tert-Butyldimethylsilyl)oxy]-6-methyl-2,8,10-dodecatrien-4-one

  摘要：

  3-Hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase inhibitors, (+)-6-epi-mevinolin (2a) and (+)-6-epi-4a,5-dihydromevinolin (2b), were prepared by combining two nonracemic units, phosphonate 3 and decalin 4, which were prepared from enantiopure 3-substituted pentanedioic acid monoesters 5a and 5b, respectively. Each acid was synthesized from cyclic anhydrides 7a and 7b by diastereoselective ring opening by means of (S)-benzyl mandelate as a common chiral auxiliary. The construction of decalin moiety 4 was accomplished by asymmetric intramolecular Diels-Alder (IMDA) reaction of nonracemic trienone 6 bearing a methyl group as a chiral controller. The IMDA diastereoselectivity of trienone 6 is discussed in terms of the configuration of(E)- and (Z)-dienophiles which are activated by an endogenous carbonyl group. The IMDA reaction of(R)-(Z)-6 under high pressure is highly selective and gives cis-decalins exclusively with preferential formation of 4 over 16. The inhibitory activity of (+)-6-epi-mevinolin (2a) and several analogs against HMG-CoA reductase was compared with mevinolin (1b). (+)-6-epi-Mevinolin (2a) was shown to be half as potent as mevinolin (1b) while (+)-6-epi-4a,5-dihydromevinolin (2b) was as potent as mevinolin.

  DOI：

  10.1021/jo970444m
• 作为产物：
  描述：

  (1Z)-1-iodo-3-(tert-butyldimethylsilyloxy)-1-propene 在 sodium hydroxide 、 正丁基锂 、 双氧水 、 溴 、 sodium methylate 、 L-Selectride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 苯 为溶剂， -100.0~25.0 ℃ 、1000.0 MPa 条件下， 反应 18.08h， 生成 (1S,3S,7S,8S,8aR)-8-(tert-Butyl-dimethyl-silanyloxymethyl)-3,7-dimethyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-ol
  参考文献：
  名称：

  Enantioselective Total Synthesis of (+)-6-epi-Mevinolin and Its Analogs. Efficient Construction of the Hexahydronaphthalene Moiety by High Pressure-Promoted Intramolecular Diels−Alder Reaction of (R,2Z,8E,10E)-1-[(tert-Butyldimethylsilyl)oxy]-6-methyl-2,8,10-dodecatrien-4-one

  摘要：

  3-Hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase inhibitors, (+)-6-epi-mevinolin (2a) and (+)-6-epi-4a,5-dihydromevinolin (2b), were prepared by combining two nonracemic units, phosphonate 3 and decalin 4, which were prepared from enantiopure 3-substituted pentanedioic acid monoesters 5a and 5b, respectively. Each acid was synthesized from cyclic anhydrides 7a and 7b by diastereoselective ring opening by means of (S)-benzyl mandelate as a common chiral auxiliary. The construction of decalin moiety 4 was accomplished by asymmetric intramolecular Diels-Alder (IMDA) reaction of nonracemic trienone 6 bearing a methyl group as a chiral controller. The IMDA diastereoselectivity of trienone 6 is discussed in terms of the configuration of(E)- and (Z)-dienophiles which are activated by an endogenous carbonyl group. The IMDA reaction of(R)-(Z)-6 under high pressure is highly selective and gives cis-decalins exclusively with preferential formation of 4 over 16. The inhibitory activity of (+)-6-epi-mevinolin (2a) and several analogs against HMG-CoA reductase was compared with mevinolin (1b). (+)-6-epi-Mevinolin (2a) was shown to be half as potent as mevinolin (1b) while (+)-6-epi-4a,5-dihydromevinolin (2b) was as potent as mevinolin.

  DOI：

  10.1021/jo970444m