(3S,4R)-3-[(R)-1-hydroxyethyl]-4-[(R)-1-methyl-3-allyloxycarbonyl-2-oxopropyl]-2-azetidinone | 107560-21-4

• 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-[(R)-1-hydroxyethyl]-4-[(R)-1-methyl-3-allyloxycarbonyl-2-oxopropyl]-2-azetidinone
• 英文别名: allyl (4R)-4-[(2R,3S)-3-{(1R)-1-hydroxyethyl}-4-oxoazetidin-2-yl]-3-oxopentanoate；prop-2-enyl (4R)-4-[(2R,3S)-3-[(1R)-1-hydroxyethyl]-4-oxoazetidin-2-yl]-3-oxopentanoate
• CAS: 107560-21-4
• 化学式: C₁₃H₁₉NO₅
• 分子量: 269.298
• InChiKey: MCDHNMTUGBVFST-JTRYMVSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  92.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,4R)-3-[(R)-1-hydroxyethyl]-4-[(R)-1-methyl-3-allyloxycarbonyl-2-oxopropyl]-2-azetidinone 以67%的产率得到
  参考文献：
  名称：

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

  摘要：

  DOI：
• 作为产物：
  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：

文献信息

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

  公开号：EP0208889A1

  公开（公告）日：1987-01-21

  Disclosed are 2-aza-substituted 1-carbadethiapen-2-em-3-carboxylic acids 1, 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 I from the known, appropriately substituted bicyclic keto ester II via the 2-azido central intermediate III: wherein R" is H or CH,, preferably beta-methyl; R6, and R7 are independently hydrogen, linear, branched or cyclic C1-C5alkyl, which can be substituted with fluoro, hydroxy, protected hydroxy, sulfoxy, amino, protected amino, wherein R' and R' taken together can also be C2-C4 alkylidene, similarly substituted; with the proviso that both R6 and R7 are not unsubstituted alkyl, R' and R2 are, inter alia, hydrogen, alkyl, acyl, and can be joined to form a ring comprising 3 to 7 atoms; Ra is hydrogen, a salt cation, a removable protecting group, or a pharmaceutically acceptable ester moiety. Also disclosed are pharmaceutical compositions comprising such compounds.

  本发明涉及2-aza取代的1-卡巴德噻吩-2-乙烯-3-羧酸1，其中通用的2-aza基团包括偶氮基、酰胺基、氨基、烷基氨基、二烷基氨基、三唑基、三唑啉基、环氧丙基和它们的药学上可接受的盐、酯、无水物和酰胺衍生物，其作为抗生素有用。还公开了从已知的适当取代的双环酮酯II通过2-偶氮中间体III制备I的过程：其中R"为H或CH，优选为β-甲基；R6和R7独立地为氢、线性、支链或环状C1-C5烷基，可被氟、羟基、保护羟基、磺酰氧基、氨基、保护氨基取代，其中R'和R'在一起也可以是C2-C4烷基亚甲基，同样被取代；条件是R6和R7都不是未取代的烷基，R'和R2是氢、烷基、酰基等，可以连接形成包含3到7个原子的环；Ra是氢、盐阳离子、可移除的保护基或药学上可接受的酯基。还公开了包含这些化合物的制药组合物。
• 3,4-disubstituted-2-azetidinone derivatives and processes for
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US05075437A1

  公开（公告）日：1991-12-24

  The invention relates to the preparation of 3,4-disubstituted-2-azetidinone compounds of the formula: ##STR1## in which R.sup.1 is hydrogen or amido-protective group, R.sup.2 is hydroxy(lower)alkyl or protected hydroxy(lower)alkyl, R.sup.3 is lower alkyl, and R.sup.4 is 1-(lower)alkyl-1-hydroxy(C.sub.2 -C.sub.6)alkyl, 1-(lower)alkyl-1-(protected hydroxy)-(C.sub.2 -C.sub.6)alkyl or 2-thioxothiazolidin-3-yl, useful as an intermediate for the production of antimicrobial agents by reacting a compound a compound of the formula: ##STR2## in which R.sup.5 is acyl, or salts thereof, with a compound of the formula: R.sup.3 --CH.sub.2 CO--R.sup.4 or salts thereof, in the presence of an enolizating agent selected from the group consisting of stannous(lower)alkylsulfonate and stannous perhalo(lower)alkylsulfonate.

  本发明涉及制备公式为：##STR1##其中R.sup.1为氢或氨基保护基，R.sup.2为羟基（低）烷基或保护羟基（低）烷基，R.sup.3为低碳基，R.sup.4为1-（低）烷基-1-羟基（C.sub.2-C.sub.6）烷基，1-（低）烷基-1-（保护羟基）-（C.sub.2-C.sub.6）烷基或2-噻唑烷酮-3-基，作为一种中间体，用于通过将公式为：##STR2##其中R.sup.5为酰基或其盐，与公式为：R.sup.3--CH.sub.2CO--R.sup.4或其盐，在选择自锡（低）烷基磺酸盐和锡卤代（低）烷基磺酸盐的羰基化试剂存在下反应，生产抗微生物剂。
• 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。
• 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：——