allyl (4R,5S,6S)-3-[(4-{(5S)-1-[(allyloxy)carbonyl]-5-methyl-2,5-dihydro-1H-pyrrol-3-yl}-1,3-thiazol-2-yl)sulfanyl]-4-methyl-7-oxo-6-{(1R)-1-[(trimethylsilyl)oxy]ethyl}-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

• 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: allyl (4R,5S,6S)-3-[(4-{(5S)-1-[(allyloxy)carbonyl]-5-methyl-2,5-dihydro-1H-pyrrol-3-yl}-1,3-thiazol-2-yl)sulfanyl]-4-methyl-7-oxo-6-{(1R)-1-[(trimethylsilyl)oxy]ethyl}-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
• 英文别名: allyl (4R,5S,6S)-3-({4-[(5S)-1-allyloxycarbonyl-5-methyl-2,5-dihydro-1H-pyrrole-3-yl]-1,3-thiazol-2-yl}thio)-4-methyl-7-oxo-6-[(1R)-1-trimethylsilyloxyethyl]-1-azabicyclo[3.2.0]hepto-2-ene-2-carboxylate；prop-2-enyl (4R,5S,6S)-4-methyl-3-[[4-[(5S)-5-methyl-1-prop-2-enoxycarbonyl-2,5-dihydropyrrol-3-yl]-1,3-thiazol-2-yl]sulfanyl]-7-oxo-6-[(1R)-1-trimethylsilyloxyethyl]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
• 化学式: C₂₈H₃₇N₃O₆S₂Si
• 分子量: 603.836
• InChiKey: XPHBJZQBSRILTN-XUKPLFAISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  152
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  allyl (4R,5S,6S)-3-[(4-{(5S)-1-[(allyloxy)carbonyl]-5-methyl-2,5-dihydro-1H-pyrrol-3-yl}-1,3-thiazol-2-yl)sulfanyl]-4-methyl-7-oxo-6-{(1R)-1-[(trimethylsilyl)oxy]ethyl}-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate 、 碳酸氢钠 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 以80%的产率得到allyl (4R,5S,6S)-3-[(4-{(5S)-1-[(allyloxy)carbonyl]-5-methyl-2,5-dihydro-1H-pyrrol-3-yl}-1,3-thiazol-2-yl)thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
  参考文献：
  名称：

  NOVEL BETA-LACTAM COMPOUNDS AND PROCESS FOR PRODUCING THE SAME

  摘要：

  公开号：

  EP1340756B1
• 作为产物：
  描述：

  allyl (2S)-4-(2-mercapto-1,3-thiazol-4-yl)-2-methyl-2,5-dihydro-1H-pyrrole-1-carboxylate 、 allyl (4R,5R,6S)-3-(diphenoxyphospholyloxy)-4-methyl-7-oxo-6-[(1R)-1-trimethylsilyloxyethyl]-1-azabicyclo[3.2.0]hepto-2-ene-2-carboxylate 在 N,N-二异丙基乙胺 、 magnesium chloride 作用下， 以 乙腈 为溶剂， 反应 3.5h， 以99%的产率得到allyl (4R,5S,6S)-3-[(4-{(5S)-1-[(allyloxy)carbonyl]-5-methyl-2,5-dihydro-1H-pyrrol-3-yl}-1,3-thiazol-2-yl)sulfanyl]-4-methyl-7-oxo-6-{(1R)-1-[(trimethylsilyl)oxy]ethyl}-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
  参考文献：
  名称：

  PROCESS FOR PRODUCTION OF B-LACTAM COMPOUND

  摘要：

  本发明公开了一种制备由公式[1]表示的碳青霉烯化合物的过程，其特征在于在公式[2]表示的化合物与公式[3]表示的化合物的反应中，允许碱和路易斯酸金属盐共存。根据该过程，在生产对革兰氏阳性菌具有优异抗菌活性的β-内酰胺化合物时，可以高效地将侧链巯基噻唑引入β-内酰胺骨架中。[3] [2] [1] 其中R1表示较低的烷基或类似物；R2表示氢原子或类似物；R3表示羧基的保护基；L表示羟基的活性酯基；R4表示氢原子或类似物；R5表示氢原子或类似物。

  公开号：

  US20100292463A1

文献信息

• Novel beta-lactam compounds and process for producing the same
  申请人：——

  公开号：US20040102433A1

  公开（公告）日：2004-05-27

  1. A &bgr;-lactam compound of the formula [1]; 1 wherein R 1 is a lower alkyl, a lower alkyl substituted by a hydroxy; R 2 is a hydrogen, a lower alkyl; X is O, S, NH; m and n are 0 to 4, Y 1 is a halogen, cyano, a hydroxy, an amino, a lower alkyloxy, a lower alkylamino, a carboxy, a carbamoyl, a lower alkyl, etc., Y 2 is hydrogen, an alkyl, cyano, —C(R 3 )═NR 4 (wherein R 3 and R 4 are hydrogen, an amino, an alkyl, etc., or R 3 and R 4 may combine each other together with the nitrogen atom to form a 5- to 7-membered heterocyclic group), or a pharmaceutically acceptable salt thereof, or a non-toxic ester thereof, which has an excellent antibacterial activity against Gram-positive bacteria, especially against MRSA and MRCNS.

  一种化学式为[1]的A &bgr;-内酰胺化合物，其中R1是低碳基，被羟基取代的低碳基; R2是氢，低碳基; X是O，S，NH; m和n为0至4，Y1是卤素，氰基，羟基，氨基，低碳基氧基，低碳基氨基，羧基，氨基甲酰基，低碳基等，Y2是氢，烷基，氰基，—C(R3)═NR4（其中R3和R4是氢，氨基，烷基等，或R3和R4可以相互结合形成5-至7成员杂环基的氮原子），或其药学上可接受的盐，或其非毒性酯，对革兰氏阳性菌，特别是对MRSA和MRCNS具有出色的抗菌活性。
• β-lactam compounds and process for producing the same
  申请人：Dainippon Sumitomo Pharma Co., Ltd.

  公开号：US07163936B2

  公开（公告）日：2007-01-16

  1. A β-lactam compound of the formula [1]; wherein R1 is a lower alkyl, a lower alkyl substituted by a hydroxy; R2 is a hydrogen, a lower alkyl; X is O, S, NH; m and n are 0 to 4, Y1 is a halogen, cyano, a hydroxy, an amino, a lower alkyloxy, a lower alkylamino, a carboxy, a carbamoyl, a lower alkyl, etc., Y2 is hydrogen, an alkyl, cyano, —C(R3)═NR4 (wherein R3 and R4 are hydrogen, an amino, an alkyl, etc., or R3 and R4 may combine each other together with the nitrogen atom to form a 5- to 7-membered heterocyclic group), or a pharmaceutically acceptable salt thereof, or a non-toxic ester thereof, which has an excellent antibacterial activity against Gram-positive bacteria, especially against MRSA and MRCNS.

  一种β-内酰胺化合物，其化学式为[1]；其中R1为较低的烷基，一种被羟基取代的较低烷基；R2为氢，较低的烷基；X为O、S、NH；m和n为0至4，Y1为卤素、氰基、羟基、氨基、较低的烷氧基、较低的烷基氨基、羧基、氨基甲酰基、较低的烷基等；Y2为氢、烷基、氰基、—C(R3)═NR4（其中R3和R4为氢、氨基、烷基等，或R3和R4可能互相结合形成一个5至7元杂环基），或其药学上可接受的盐或非毒性酯，对革兰氏阳性菌，特别是MRSA和MRCNS具有优异的抗菌活性。
• NOVEL BETA-LACTAM COMPOUNDS AND PROCESS FOR PRODUCING THE SAME
  申请人：Dainippon Sumitomo Pharma Co., Ltd.

  公开号：EP1340756B1

  公开（公告）日：2007-10-10
• PROCESS FOR PRODUCTION OF B-LACTAM COMPOUND
  申请人：Watanabe Shoji

  公开号：US20100292463A1

  公开（公告）日：2010-11-18

  Disclosed is a process for producing a carbapenem compound represented by Formula [1], which is characterized by allowing a base and a Lewis acid metal salt to coexist in the reaction of a compound represented by Formula [2] with a compound represented by Formula [3]. According to the process, a side-chain mercaptothiazole can be introduced into a β-lactam skeleton efficiently in the production of a β-lactam compound having an excellent antibacterial activity against a Gram-positive bacterium. [3] [2] [1] wherein R 1 represents a lower alkyl group or the like; R 2 represents hydrogen atom or the like; R 3 represents a protective group for a carboxyl group; L represents an active ester of a hydroxy group; R 4 represents hydrogen atom or the like; and R 5 represents hydrogen atom or the like.

  本发明公开了一种制备由公式[1]表示的碳青霉烯化合物的过程，其特征在于在公式[2]表示的化合物与公式[3]表示的化合物的反应中，允许碱和路易斯酸金属盐共存。根据该过程，在生产对革兰氏阳性菌具有优异抗菌活性的β-内酰胺化合物时，可以高效地将侧链巯基噻唑引入β-内酰胺骨架中。[3] [2] [1] 其中R1表示较低的烷基或类似物；R2表示氢原子或类似物；R3表示羧基的保护基；L表示羟基的活性酯基；R4表示氢原子或类似物；R5表示氢原子或类似物。