ethyl 2-[(1R,2R,6S)-2-{(R)-5-benzyloxyhexyl}-6-(tert-butyldimethylsilyloxy)-3-oxocyclohexyl]acetate | 960492-25-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 2-[(1R,2R,6S)-2-{(R)-5-benzyloxyhexyl}-6-(tert-butyldimethylsilyloxy)-3-oxocyclohexyl]acetate
• 英文别名: ethyl 2-[(1R,2R,6S)-6-[tert-butyl(dimethyl)silyl]oxy-3-oxo-2-[(5R)-5-phenylmethoxyhexyl]cyclohexyl]acetate
• CAS: 960492-25-5
• 化学式: C₂₉H₄₈O₅Si
• 分子量: 504.783
• InChiKey: IGICXTDBDXCGIR-YUHKXCSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.09
• 重原子数：
  35
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 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：

  ethyl 2-[(1R,2R,6S)-2-{(R)-5-benzyloxyhexyl}-6-(tert-butyldimethylsilyloxy)-3-oxocyclohexyl]acetate 在 palladium on activated charcoal 偶氮二甲酸二异丙酯 、 potassium trimethylsilonate 、 氢气 、 三苯基膦 作用下， 以 四氢呋喃 、 乙酸乙酯 、 甲苯 为溶剂， 反应 19.5h， 生成 (-)-{(1R,2R,6S)-6-(tert-butyldimethylsilyloxy)-2-[(S)-5-hydroxyhexyl]-3-oxo-cyclohex-1-yl}acetic acid lactone
  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：

  (R)-2-benzyloxy-6-iodohexane 、 ethyl 2-[(1R,6S)-3,6-bis[[tert-butyl(dimethyl)silyl]oxy]cyclohex-2-en-1-yl]acetate 在 tris(dimethylamino)sulfonium difluorotrimrthyl-siliconate 作用下， 反应 16.0h， 以73%的产率得到ethyl 2-[(1R,2R,6S)-2-{(R)-5-benzyloxyhexyl}-6-(tert-butyldimethylsilyloxy)-3-oxocyclohexyl]acetate
  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.