(3S,4R)-3-<(1R)-1-tert-butyldimethylsilyloxyethyl>-4-<(1R)-3-allyloxycarbonyl-1-methyl-2-oxopropyl>azetidin-2-one | 107560-20-3

• 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-butyldimethylsilyloxyethyl>-4-<(1R)-3-allyloxycarbonyl-1-methyl-2-oxopropyl>azetidin-2-one
• 英文别名: (3S,4R)-3-((1R)-1-tert-butyldimethylsilyloxyethyl)-4-((1R)-3-allyloxycarbonyl-1-methyl-2-oxopropyl)azetidin-2-one；(3S,4R)-3-[(R)-1-t-butyldimethylsilyloxyethyl]-4-[(R)-1-methyl-3-allyloxycarbonyl-2-oxopropyl]-2-azetidinone；prop-2-enyl (4R)-4-[(2R,3S)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl]-3-oxopentanoate
• CAS: 107560-20-3
• 化学式: C₁₉H₃₃NO₅Si
• 分子量: 383.56
• InChiKey: OHFXJIZYEKBAQX-NSNWQYSKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,4R)-3-<(1R)-1-tert-butyldimethylsilyloxyethyl>-4-<(1R)-3-allyloxycarbonyl-1-methyl-2-oxopropyl>azetidin-2-one 生成 (3S,4R)-3-[(R)-1-hydroxyethyl]-4-[(R)-1-methyl-3-allyloxycarbonyl-2-oxopropyl]-2-azetidinone
  参考文献：
  名称：

  CHRISTENSEN, BURTON G.;RATCLIFFE, RONALD W.;CHABALA, JOHN C.

  摘要：

  DOI：
• 作为产物：
  描述：

  4-乙酰氧基氮杂环丁酮 在 正丁基锂 、 sodium hydride 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 18.0h， 生成 (3S,4R)-3-<(1R)-1-tert-butyldimethylsilyloxyethyl>-4-<(1R)-3-allyloxycarbonyl-1-methyl-2-oxopropyl>azetidin-2-one
  参考文献：
  名称：

  1-β-Methylcarbapenem intermediates. Stereoselective synthesis of (3S,4R)-3-[(1R)-1-tert-butyldimethylsilyloxyethyl]-4-[(1R)-3-methoxycarbonyl-1-methyl-2-oxopropyl]azetidin-2-one and its related chemistry

  摘要：

  通过在金属盐存在下，4-乙酰氧基氮杂环丁酮 3a 和 3-氧代戊酸酯 12 或 13 的二负离子（或相应的双硅烯醇醚）之间的立体选择性醛缩反应制备了携带1-β-甲基基团（14a）的手性中间体，用于合成1-β-甲基卡巴比林类抗生素（1）。同时还揭示了一个主要的副反应。

  DOI：

  10.1139/v88-226

文献信息

• 2-aza-substituted 1-carbadethiapen-2-em-3-carboxylic acids
  申请人：Merck & Co., Inc.

  公开号：US04833167A1

  公开（公告）日：1989-05-23

  Disclosed are 2-aza-substituted 1-carbadethiapen-2-em-3-carboxylic acids I, where the generic 2-aza group includes azido, acylamino, amino, alkylamino, diaklylamino, triazolyl, triazolinyl, aziridinyl, and their pharmaceutically acceptable salt, ester, anhydride and amide derivatives which are useful as antibiotics. Also disclosed are processes for the preparation of I from the known, appropriately substituted bicyclic keto ester II via the 2-azido central intermediate III: ##STR1## wherein R.sup.16 is H or CH.sub.3, preferably beta-methyl; R.sup.6, and R.sup.7 are independently hydrogen, linear, branched or cyclic C.sub.1 -C.sub.5 alkyl, which can be substituted with fluoro, hydroxy, protected hydroxy, sulfoxy, amino, protected amino wherein R.sup.6 and R.sup.7 taken together can also be C.sub.2 -C.sub.4 alkylidene, similarly substituted; with the proviso that both R.sup.6 and R.sup.7 are not unsubstituted alkyl, R.sup.1 and R.sup.2 are, inter alia, hydrogen, alkyl, acyl, and can be joined to form a ring comprising 3 to 7 atoms; R.sup.a is hydrogen, a salt cation, a removable protecting group, or a pharmaceutically acceptable ester moiety. Also disclosed are processes for the preparation of such compounds; pharmaceutical compositions comprising such compounds; and methods of treatment comprising administering such compounds and compositions when an antibiotic effect is indicated.

  本发明涉及2-氮代取代的1-卡巴德硫杂戊烯-2-烯-3-羧酸I，其中通用的2-氮代基包括叠氮基，酰胺基，氨基，烷基氨基，二烷基氨基，三唑基，三唑啉基，环氧乙烷基，并且它们的药学上可接受的盐，酯，无水物和酰胺衍生物，可用作抗生素。本发明还公开了从已知的适当取代的双环酮酯II通过2-叠氮中间体III制备I的工艺：其中R.sup.16为H或CH.sub.3，优选为β-甲基；R.sup.6和R.sup.7分别为氢，线性，支链或环状C.sub.1-C.sub.5烷基，可以被氟，羟基，保护羟基，磺氧基，氨基，保护氨基取代，其中R.sup.6和R.sup.7一起也可以是C.sub.2-C.sub.4烷基亚甲基，类似取代；但要求R.sup.6和R.sup.7均不是未取代的烷基，R.sup.1和R.sup.2是，例如，氢，烷基，酰基，并且可以连接成包含3到7个原子的环；R.sup.a是氢，盐阳离子，可去除的保护基或药学上可接受的酯基。本发明还公开了制备这种化合物的方法；包含这种化合物的制药组合物；以及在需要抗生素作用时，给予这种化合物和组合物的治疗方法。
• 3-pyrrolidinylthio-1-azabicyclo(3.2.0)-hept-2-ene-2-carboxylic acid
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US04822787A1

  公开（公告）日：1989-04-18

  This invention consists of 3-pyrrolidinylthio-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid compounds and their use as antimicrobial agents in the treatment of infectious diseases.

  这项发明涉及3-吡咯烷基硫基-1-氮杂双环[3.2.0]庚-2-烯-2-羧酸化合物及其在治疗传染病中作为抗微生物药物的用途。
• 2-aza substituted-1-carbadethiapen-2-em-3-carboxylic acids
  申请人：Merck & Co., Inc.

  公开号：US04892869A1

  公开（公告）日：1990-01-09

  Disclosed are 2-aza-substituted 1-carbadethiapen-2-em-3-carboxylic acids I, where the generic 2-aza group includes azido, acylamino, amino, alkylamino, dialkylamino, triazolyl, triazolinyl, aziridinyl, and their pharmaceutically acceptable salt, ester, anhydride and amide derivatives which are useful as antibiotics. Also disclosed are processes for the preparation of 1 from the known, appropriately substituted bicyclic keto ester II via the 2-azido central intermediate III: ##STR1## wherein R.sup.16 is H or CH.sub.3, preferably beta-methyl; R.sup.6, and R.sup.7 are independently hydrogen, linear, branched or cyclic C.sub.1 -C.sub.5 alkyl, which can be substituted with fluoro, hydroxy, protected hydroxy, sulfoxy, amino, protected amino, wherein R.sup.6 and R.sup.7 taken together can also be C.sub.2 -C.sub.4 alkylidene, similarly substituted; with the proviso that both R.sup.6 and R.sup.7 are not unsubstituted alkyl, R.sup.1 and R.sup.2 are, inter alia, hydrogen, alkyl, acyl, and can be joined to form a ring comprising 3 to 7 atoms; R.sup.a is hydrogen, a salt cation, a removable protecting group, or a pharmaceutically acceptable ester moiety. Also disclosed are processes for the preparation of such compounds; pharmaceutical compositions comprising such compounds; and methods of treatment comprising administering such compounds and compositions when an antibiotic effect is indicated.

  本发明涉及2-aza取代的1-carbadethiapen-2-em-3-羧酸I，其中通用的2-aza基团包括azido，acylamino，氨基，烷基氨基，二烷基氨基，三唑基，三唑啉基，环氧乙烷基，以及它们的药学上可接受的盐，酯，酸酐和酰胺衍生物，它们可用作抗生素。还公开了从已知的适当取代的双环酮酯II经2-azido中间体III制备1的过程：其中R16是H或CH3，优选为β-甲基；R6和R7分别是氢，线性，支链或环状C1-C5烷基，可以用氟，羟基，保护羟基，磺酸基，氨基，保护氨基替代，R6和R7取在一起也可以是C2-C4烷基亚甲基，同样取代；但前提是R6和R7都不是未取代的烷基，R1和R2是氢，烷基，酰基等，可以结合形成包含3到7个原子的环；Ra是氢，盐阳离子，可去除的保护基或药学上可接受的酯基。还公开了制备这种化合物的方法；包含这种化合物的制药组合物；以及在抗生素效应指示时，给予这种化合物和组合物的治疗方法。
• CHRISTENSEN, BURTON G.;RATCLIFFE, RONALD W.;CHABALA, JOHN C.
  作者：CHRISTENSEN, BURTON G.、RATCLIFFE, RONALD W.、CHABALA, JOHN C.

  DOI：——

  日期：——
• CHRISTENSEN, BURTON G.;CHABALA, JOHN C.;RATCLIFFE, RONALD W.
  作者：CHRISTENSEN, BURTON G.、CHABALA, JOHN C.、RATCLIFFE, RONALD W.

  DOI：——

  日期：——