(4R,8aR,12S,12aR)-12-(tert-butyldimethylsilyloxy)-4-methyloctahydro-1H-benzo[d]oxecine-2,9(10H,11H)-dione | 960492-30-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 奥昔康唑
• 英文名称: (4R,8aR,12S,12aR)-12-(tert-butyldimethylsilyloxy)-4-methyloctahydro-1H-benzo[d]oxecine-2,9(10H,11H)-dione
• 英文别名: (4R,8aR,12S,12aR)-12-[tert-butyl(dimethyl)silyl]oxy-4-methyl-4,5,6,7,8,8a,10,11,12,12a-decahydro-1H-benzo[d]oxecine-2,9-dione
• CAS: 960492-30-2
• 化学式: C₂₀H₃₆O₄Si
• 分子量: 368.589
• InChiKey: OKQHBMSKXVMDHM-KONPQCLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.87
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R,8aR,12S,12aR)-12-(tert-butyldimethylsilyloxy)-4-methyloctahydro-1H-benzo[d]oxecine-2,9(10H,11H)-dione 在 palladium diacetate sodium hexamethyldisilazane 、 三乙基氯硅烷 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 72.75h， 以70%的产率得到(4R,8aR,12S,12aR)-12-(tert-butyldimethylsilyloxy)-4-methyl-4,5,6,7,8,8a-hexahydro-1H-benzo[d]oxecine-2,9(12H,12aH)-dione
  参考文献：
  名称：

  Stereoselective synthesis of the bacterial DNA primase inhibitor Sch 642305 and its C-4 epimer

  摘要：

  A convergent stereoselective synthesis of the bacterial DNA primase inhibitor Sch 642305 and its non-natural epimer at C-4 is described. A key aspect was the construction of a trans-2,3-disubstituted cyclohexanone system by means of a stereoselective Michael addition/alpha-alkylation sequence. The macrolactone ring of either stereoisorner was created using the Mitsunobu and Yamaguchi procedures, respectively. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.09.080
• 作为产物：
  描述：

  ethyl 2-[(1R,2R,6S)-2-{(R)-5-benzyloxyhexyl}-6-(tert-butyldimethylsilyloxy)-3-oxocyclohexyl]acetate 在 palladium on activated charcoal 4-二甲氨基吡啶 、 2,4,6-三氯苯甲酰氯 、 potassium trimethylsilonate 、 氢气 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 22.0h， 生成 (4R,8aR,12S,12aR)-12-(tert-butyldimethylsilyloxy)-4-methyloctahydro-1H-benzo[d]oxecine-2,9(10H,11H)-dione
  参考文献：
  名称：

  Stereoselective synthesis of the bacterial DNA primase inhibitor Sch 642305 and its C-4 epimer

  摘要：

  A convergent stereoselective synthesis of the bacterial DNA primase inhibitor Sch 642305 and its non-natural epimer at C-4 is described. A key aspect was the construction of a trans-2,3-disubstituted cyclohexanone system by means of a stereoselective Michael addition/alpha-alkylation sequence. The macrolactone ring of either stereoisorner was created using the Mitsunobu and Yamaguchi procedures, respectively. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.09.080

文献信息

• Stereoselective synthesis of the bacterial DNA primase inhibitor Sch 642305 and its C-4 epimer
  作者：Jorge García-Fortanet、Miguel Carda、J. Alberto Marco

  DOI：10.1016/j.tet.2007.09.080

  日期：2007.12

  A convergent stereoselective synthesis of the bacterial DNA primase inhibitor Sch 642305 and its non-natural epimer at C-4 is described. A key aspect was the construction of a trans-2,3-disubstituted cyclohexanone system by means of a stereoselective Michael addition/alpha-alkylation sequence. The macrolactone ring of either stereoisorner was created using the Mitsunobu and Yamaguchi procedures, respectively. (c) 2007 Elsevier Ltd. All rights reserved.