(-)-{(1R,2R,6S)-6-(tert-butyldimethylsilyloxy)-2-[(S)-5-hydroxyhexyl]-3-oxo-cyclohex-1-yl}acetic acid lactone | 935473-71-5

• 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: (-)-{(1R,2R,6S)-6-(tert-butyldimethylsilyloxy)-2-[(S)-5-hydroxyhexyl]-3-oxo-cyclohex-1-yl}acetic acid lactone
• 英文别名: (4S,8aR,12S,12aR)-12-(tert-butyldimethylsilyloxy)-4-methyloctahydro-1H-benzo[d]oxecine-2,9(10H,11H)-dione；(4S,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: 935473-71-5
• 化学式: C₂₀H₃₆O₄Si
• 分子量: 368.589
• InChiKey: OKQHBMSKXVMDHM-LHHMISFZSA-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：

  (-)-{(1R,2R,6S)-6-(tert-butyldimethylsilyloxy)-2-[(S)-5-hydroxyhexyl]-3-oxo-cyclohex-1-yl}acetic acid lactone 在 四丁基氟化铵 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 72.75h， 生成 (4S,8aR,12S,12aR)-12-hydroxy-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：

  在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以118 mg的产率得到(-)-{(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

文献信息

• Concise Synthesis of the Bacterial DNA Primase Inhibitor (+)-Sch 642305
  作者：Erica M. Wilson、Dirk Trauner

  DOI：10.1021/ol070173u

  日期：2007.3.1

  A highly convergent, enantioselective synthesis of (+)-Sch 642305 is presented, which features a Mukaiyama-Michael addition followed by allylation to establish the syn-anti relationship of the three contiguous stereocenters. The 10-membered macrolactone was formed through ring-closing metathesis.
• 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.