1-(t-butyldimethylsilyl)-4-(triphenylmethylthio)azetidin-2-one | 75939-53-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1-(t-butyldimethylsilyl)-4-(triphenylmethylthio)azetidin-2-one
• 英文别名: 1-(tert-buthyldimethylsilyl)-4-tritylthio-2-azetidinone；1-(t-butyldimethylsilyl)-4-tritylthio-2-azetidinone；1-t-Butyldimethylsilyl-4-tritylthio-2-azetidinone；1-[tert-butyl(dimethyl)silyl]-4-tritylsulfanylazetidin-2-one
• CAS: 75939-53-6
• 化学式: C₂₈H₃₃NOSSi
• 分子量: 459.728
• InChiKey: ZISQMZNAYGXRTB-UHFFFAOYSA-N

物化性质

• 沸点：
  530.9±50.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.28
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  45.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(t-butyldimethylsilyl)-4-(triphenylmethylthio)azetidin-2-one 在 吡啶 、 甲醇 、 正丁基锂 、 四丁基氟化铵 、 溶剂黄146 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.0h， 生成 (3S^*,4R^*)-3-(4-methyl-2-oxo-1,3-dioxolan-4-yl)-4-triphenylmethylthio-2-azetidinoneio-2-azetidinone
  参考文献：
  名称：

  Carbapenem and penem antibiotics. III. Synthesis and antibacterial activity of 2-functionalized-methyl penems related to asparenomycins.

  摘要：

  合成了具有C-6位1-(羟甲基)亚乙基或环状碳酸酯侧链的R构型和光学活性2-(杂芳基)硫代甲基青霉烯（24、51、63、65、37、40、69以及21b、61b、26b、30b、64b、35b、66b、39b、68b），并测定了它们的抗菌活性。

  DOI：

  10.1248/cpb.33.4371
• 作为产物：
  描述：

  4-(triphenylmethylthio)azetidin-2-one 生成 1-(t-butyldimethylsilyl)-4-(triphenylmethylthio)azetidin-2-one
  参考文献：
  名称：

  MENARD, M.;MARTEL, A.

  摘要：

  DOI：

文献信息

• 2,6-Disubstituted penem compounds
  申请人：Bristol-Myers Company

  公开号：US04282150A1

  公开（公告）日：1981-08-04

  This invention relates to 2-substituted and 2,6-disubstituted penem compounds of the formula ##STR1## wherein Y is hydrogen, halo or certain organic radicals and X represents certain hetero-interrupted substituted alkyl radicals. Also included in the invention are pharmaceutically acceptable salts of the above compounds and derivatives of the above compounds in which the carboxyl group at the 3-position is protected as by an easily removable ester protecting group. The compounds of the present invention are potent antibacterial agents or are of use as intermediates in the preparation of such agents.

  本发明涉及2-取代和2,6-二取代的戊二烯化合物，其化学公式如下：##STR1## 其中Y代表氢，卤素或某些有机基团，X代表某些杂原子打断的取代烷基基团。发明还包括上述化合物的药用可接受盐，以及上述化合物的衍生物，其中3位上的羧基被易于移除的酯保护基团所保护。本发明的化合物是强效的抗菌剂，或者可用作制备此类药物的中间体。
• Antibacterial agents, and 4-thio azetidinone intermediates
  申请人：Bristol-Myers Company

  公开号：US04272437A1

  公开（公告）日：1981-06-09

  This invention relates to 2-substituted and 2,6-disubstituted penem compounds of the formula ##STR1## wherein Y is hydrogen, halo or certain organic substituents and X represents certain organic substituents. Also included in the invention are pharmaceutically acceptable salts of the above compounds and derivatives of the above compounds in which the carboxyl group at the 3-position is protected as by an easily removable ester protecting group. The compounds of the present invention are potent antibacterial agents or are of use as intermediates in the preparation of such agents.

  本发明涉及2-取代和2,6-二取代的青霉烯化合物，其公式为##STR1##，其中Y是氢、卤素或某些有机取代基，X代表某些有机取代基。发明还包括上述化合物的药用可接受盐和上述化合物的衍生物，其中3位的羧基被易于移除的酯保护基团所保护。本发明的化合物是强效的抗菌剂，或可用于制备此类药物的中间体。
• Preparation of 3-benzoylpenems and penem amides by wittig methodology
  作者：Neil D Pearson、Terence C Smale、Robert Southgate

  DOI：10.1016/0040-4039(95)00767-7

  日期：1995.6

  Condensation of phenyl glyoxal with azetidin-2-ones (1a-c) gave the hemi-aminals (2a-c). Subsequent conversions produced the 4-(formylthio)phosphoranes (4a-c) which gave on heating the 3-benzoylpenems (5a-c), formed by intramolecular Wittig cyclisation. Thermal isomerisation of trans-6-substituted-3-benzoylpenems allowed the preparation of the cis-6-substituted-3-benzoylpenems (7a-c). Using similar

  苯乙二醛与氮杂环丁烷-2-酮（1a-c）的缩合得到半缩醛（2a-c）。随后的转化产生了4-（甲硫基）膦酸酯（4a-c），其通过加热通过分子内维蒂希环化形成了3-苯甲酰基penems（5a-c）。反式-6取代的-3-苯甲酰基青霉烯的热异构化允许制备顺式-6取代的-3-苯甲酰基青霉烯（7a-c）。使用相似的方法，合成了戊烯酰胺（7d-e）。
• Nuclear analogs of β-lactam antibiotics. XVI. Aldol condensations of N-protected 4-tritylthio-2-azetidinones
  作者：Alain Martel、Jean Collerette、Jacques Banville、Jean-Paul Daris、Philippe Lapointe、Bernard Belleau、Marcel Ménard

  DOI：10.1139/v83-111

  日期：1983.3.1

  The reaction of acetaldehyde with enolates of N-protected 4-tritylthio-2-azetidinones 4b and 4c was studied. While the lithium enolate of N-methoxymethylazetidinone 4b gave only transS* 3-(1′-hydroxyethyl)azetidinone 8 the corresponding tetrabutylammonium enolate gave a mixture of transR* and transS* azetidinones 8 and 9. The metal enolate of N-(tert-butyldimethylsilyl)-4-tritylthio-2-azetidinone 4c gave all four possible isomers.

  对N-保护的4-三苄硫基-2-氮杂环戊酮4b和4c的烯醇酸醛反应进行了研究。虽然N-甲氧甲基氮杂环戊酮4b的锂烯醇只产生了transS* 3-(1'-羟基乙基)氮杂环戊酮8，但相应的四丁基铵烯醇产生了transR*和transS*氮杂环戊酮8和9的混合物。N-(叔丁基二甲基硅基)-4-三苄硫基-2-氮杂环戊酮4c的金属烯醇产生了所有四种可能的异构体。
• 4-Acylthioazetidinone intermediates for antibacterial agents
  申请人：Bristol-Myers Company

  公开号：US04461727A1

  公开（公告）日：1984-07-24

  This invention relates to 2-substituted and 2,6-disubstituted penem compounds of the formula ##STR1## wherein Y is hydrogen, halo or certain organic radicals and X represents certain hetero-interrupted substituted alkyl radicals. Also included in the invention are pharmaceutically acceptable salts of the above compounds and derivatives of the above compounds in which the carboxyl group at the 3-position is protected as by an easily removable ester protecting group. The compounds of the present invention are potent antibacterial agents or are of use as intermediates in the preparation of such agents.

  本发明涉及公式为##STR1##的2-取代和2,6-二取代的青霉烷化合物，其中Y为氢、卤素或某些有机基团，X代表某些杂原子中断的取代烷基基团。本发明还包括上述化合物的药学上可接受的盐和上述化合物的衍生物，其中3位的羧基被易于去除的酯保护基所保护。本发明的化合物是强效的抗菌剂或用于制备这种剂的中间体。