(3S,4R)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<(1R)-1-<((4S)-4-ethyl-2-thioxo-1,3-thiazolidin-3-yl)carbonyl>ethyl>azetidin-2-one | 109267-65-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (3S,4R)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<(1R)-1-<((4S)-4-ethyl-2-thioxo-1,3-thiazolidin-3-yl)carbonyl>ethyl>azetidin-2-one
• 英文别名: (3S,4R)-3-{(1R)-1-[(tert-Butyldimethylsilyl)oxy]ethyl}-4-{(1R)-1-[((4S)-4-ethyl-2-thioxo-1,3-thiazolidin-3-yl)carbonyl]ethyl}azetidin-2-one；(3S,4R)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-[(2R)-1-[(4S)-4-ethyl-2-sulfanylidene-1,3-thiazolidin-3-yl]-1-oxopropan-2-yl]azetidin-2-one
• CAS: 109267-65-4
• 化学式: C₁₉H₃₄N₂O₃S₂Si
• 分子量: 430.708
• InChiKey: QKOCUPTYCFNXGA-UXXRCYHCSA-N

物化性质

• 熔点：
  85-86.5 °C
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.79
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  58.64
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (3S,4R)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<(1R)-1-<((4S)-4-ethyl-2-thioxo-1,3-thiazolidin-3-yl)carbonyl>ethyl>azetidin-2-one 以 乙腈 为溶剂， 反应 5.5h， 生成 (3S,4R)-3-<(1R)-1-t-butyldimethylsilyloxyethyl>-4-<(1R)-1-methyl-3-p-nitrobenzyloxycarbonyl-2-oxopropyl>-2-azetidin-2-one
  参考文献：
  名称：

  .beta.-Lactams. 3. Asymmetric total synthesis of new non-natural 1.beta.-methylcarbapenems exhibiting strong antimicrobial activities and stability against human renal dehydropeptidase-I

  摘要：

  Asymmetric synthesis of 11, the precursor to chiral (3R,4R)-3-[(1R)-1-[(tert-butyldimethylsilyl)oxy]ethyl]-4-acetoxyazetidin-2-one (3) was achieved by utilizing a highly diastereoselective aldol-type reaction of acetaldehyde and the chiral tin(II) enolate of 5. Similar diastereoselective alkylations of chiral and achiral tin(II) enolates 13a-d with chiral 3 were also performed to obtain the desired alkylated azetidin-2-ones (17a-d). Compounds 17a,b were successfully converted to new, non-natural 1-beta-methylcarbapenems 1a and 1b, which exhibited strong and wide-ranging antimicrobial activities and excellent stability against human renal dehydropeptidase-I.

  DOI：

  10.1021/jo00041a033
• 作为产物：
  描述：

  4-乙酰氧基氮杂环丁酮 、 3-Propionyl-(4S)-ethyl-1,3-thiazolidine-2-thione 在 N-乙基哌啶 、 tin(II) trifluoromethanesulfonate 作用下， 生成 (3S,4R)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<(1R)-1-<((4S)-4-ethyl-2-thioxo-1,3-thiazolidin-3-yl)carbonyl>ethyl>azetidin-2-one
  参考文献：
  名称：

  Highly diastereoselective alkylation onto 4-acetoxy-2-azetidinones employing tin(II) enolates of 3-acyl C-4-chiral 1,3-thiazolidine-2-thiones

  摘要：

  DOI：

  10.1021/ja00275a082

文献信息

• NAGAO, JOSIMITSU;KUMAGAYA, TOSIO;TAMAI, CATOPY;KYPAMOTO, YASUXIRO;SIMIDZU+
  作者：NAGAO, JOSIMITSU、KUMAGAYA, TOSIO、TAMAI, CATOPY、KYPAMOTO, YASUXIRO、SIMIDZU+

  DOI：——

  日期：——
• MATSUNAGA, XIROSI;TAMAI, SATORU;KOBAYASI, SIGEHAKI;KUMAGAYA, TOSIO;NAGASE+
  作者：MATSUNAGA, XIROSI、TAMAI, SATORU、KOBAYASI, SIGEHAKI、KUMAGAYA, TOSIO、NAGASE+

  DOI：——

  日期：——
• AOYANAGI, SAKAEH;KOBAYASI, SIGEHAKI
  作者：AOYANAGI, SAKAEH、KOBAYASI, SIGEHAKI

  DOI：——

  日期：——
• KUMAGAI, TOSIO;MATSUNAGA, XIROSI;MATIDA, JOSISUKEH;NAGASEH, YUNOSUKEH;XIK+
  作者：KUMAGAI, TOSIO、MATSUNAGA, XIROSI、MATIDA, JOSISUKEH、NAGASEH, YUNOSUKEH、XIK+

  DOI：——

  日期：——
• KOBAYASI, SIGEHAKI;AOYANAGI, SAKAEH;NAGASEH, YUNOSUKEH;XIKIDA, MUNEHO;NAG+
  作者：KOBAYASI, SIGEHAKI、AOYANAGI, SAKAEH、NAGASEH, YUNOSUKEH、XIKIDA, MUNEHO、NAG+

  DOI：——

  日期：——