(-)-{(1R,2R,6S)-6-(tert-butyldimethylsilyloxy)-2-[(S)-5-hydroxy-hex-2-enyl]-3-oxo-cyclohex-1-yl}acetic acid lactone | 935473-70-4

• 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-hydroxy-hex-2-enyl]-3-oxo-cyclohex-1-yl}acetic acid lactone
• 英文别名: (4S,6Z,8aR,12S,12aR)-12-[tert-butyl(dimethyl)silyl]oxy-4-methyl-4,5,8,8a,10,11,12,12a-octahydro-1H-3-benzoxecine-2,9-dione
• CAS: 935473-70-4
• 化学式: C₂₀H₃₄O₄Si
• 分子量: 366.573
• InChiKey: XMIXZJGOLHAOBF-QEKHZTQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.64
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 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-hydroxy-hex-2-enyl]-3-oxo-cyclohex-1-yl}acetic acid lactone 在 palladium on activated charcoal palladium diacetate 、 氢气 作用下， 以 四氢呋喃 、 乙酸乙酯 、 乙腈 为溶剂， 反应 26.5h， 生成 (+)-O-(tert-butyldimethylsilyl)Sch 642305
  参考文献：
  名称：

  Concise Synthesis of the Bacterial DNA Primase Inhibitor (+)-Sch 642305

  摘要：

  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.

  DOI：

  10.1021/ol070173u
• 作为产物：
  描述：

  在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 4 A molecular sieve 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.5h， 生成 (-)-{(1R,2R,6S)-6-(tert-butyldimethylsilyloxy)-2-[(S)-5-hydroxy-hex-2-enyl]-3-oxo-cyclohex-1-yl}acetic acid lactone
  参考文献：
  名称：

  Concise Synthesis of the Bacterial DNA Primase Inhibitor (+)-Sch 642305

  摘要：

  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.

  DOI：

  10.1021/ol070173u

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.