4-Nitrobenzyl (1R,5S,6S)-2-{(3S,5S)-5-[3(S)-(4-nitrobenzyloxycarbonyl)aminopyrrolidin-1-ylcarbonyl]-1-methylpyrrolidin-3-ylthio}-6-[1(R)-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate | 147082-50-6

• 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: 4-Nitrobenzyl (1R,5S,6S)-2-{(3S,5S)-5-[3(S)-(4-nitrobenzyloxycarbonyl)aminopyrrolidin-1-ylcarbonyl]-1-methylpyrrolidin-3-ylthio}-6-[1(R)-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate
• 英文别名: 4-Nitrobenzyl (1R,5S.6S)-2-{(3S,5S)-5-[3(S)-(4-nitrobenzyloxycarbonyl)aminopyrrolidin-1-ylcarbonyl]-1-methylpyrrolidin-3-ylthio}-6-[1(R)-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate；4-Nitrobenzyl (1R, 5S,6S)-2-[(3S,5S)-5-[3-(S)-(4-nitrobenzyloxycarbonyl)aminopyrrolidin-1-ylcarbonyl]-1-methylpyrrolidin-3-ylthio)-6-[1(R)-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate；(4-nitrophenyl)methyl (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3-[(3S,5S)-1-methyl-5-[(3S)-3-[(4-nitrophenyl)methoxycarbonylamino]pyrrolidine-1-carbonyl]pyrrolidin-3-yl]sulfanyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
• CAS: 147082-50-6
• 化学式: C₃₅H₄₀N₆O₁₁S
• 分子量: 752.802
• InChiKey: JBOSPUHFNXNVPI-IJIGBHEVSA-N

物化性质

• 沸点：
  961.0±65.0 °C(predicted)
• 密度：
  1.49±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  53
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  246
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  4-Nitrobenzyl (1R,5S,6S)-2-{(3S,5S)-5-[3(S)-(4-nitrobenzyloxycarbonyl)aminopyrrolidin-1-ylcarbonyl]-1-methylpyrrolidin-3-ylthio}-6-[1(R)-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 (4R,5S,6S)-3-[(3S,5S)-5-[(3S)-3-aminopyrrolidine-1-carbonyl]-1-methylpyrrolidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and Antibacterial Activity of Novel 1.BETA.-Methyl Carbapenems with Cycloalkylamine Moiety at the C-2 Position.

  摘要：

  具有环烷基胺侧链的新型1β-甲基碳青霉烯类化合物被合成，并研究了它们的构效关系。这些碳青霉烯类化合物对广泛的革兰氏阳性和革兰氏阴性细菌展现出强大的抗菌活性，并且在小鼠腹腔给药时具有中等程度的尿液回收率。

  DOI：

  10.7164/antibiotics.54.1080
• 作为产物：
  描述：

  氯甲酸对硝基苄酯 在 三氟甲磺酸 、 苯甲醚 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 、 三氟乙酸 为溶剂， 生成 4-Nitrobenzyl (1R,5S,6S)-2-{(3S,5S)-5-[3(S)-(4-nitrobenzyloxycarbonyl)aminopyrrolidin-1-ylcarbonyl]-1-methylpyrrolidin-3-ylthio}-6-[1(R)-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate
  参考文献：
  名称：

  Synthesis and Antibacterial Activity of Novel 1.BETA.-Methyl Carbapenems with Cycloalkylamine Moiety at the C-2 Position.

  摘要：

  具有环烷基胺侧链的新型1β-甲基碳青霉烯类化合物被合成，并研究了它们的构效关系。这些碳青霉烯类化合物对广泛的革兰氏阳性和革兰氏阴性细菌展现出强大的抗菌活性，并且在小鼠腹腔给药时具有中等程度的尿液回收率。

  DOI：

  10.7164/antibiotics.54.1080

文献信息

• Azetidinone compounds useful in the preparation of carbapenem
  申请人：Sankyo Company, Limited

  公开号：US05541317A1

  公开（公告）日：1996-07-30

  Compounds of formula (I): ##STR1## wherein: R.sup.1 is hydrogen or a hydroxy-protecting group; R.sup.2 is alkyl, alkoxy, halogen, optionally substituted phenyl or optionally substituted phenoxy; R.sup.3 is optionally substituted pyridyl, optionally substituted quinolyl or phenyl group which has a substituent of formula --CYNR.sup.5 R.sup.6, where Y is oxygen or sulfur, and R.sup.5 and R.sup.6 are each alkyl, aryl or aralkyl, or R.sup.5 and R.sup.6 and the nitrogen to which they are attached together form a heterocyclic group; is R.sup.4 hydrogen or an amino-protecting group; and Z is sulfur or oxygen; are valuable intermediates in the preparation of carbapenem compounds and retain a desirable configuration during conversion to such carbapenem compounds. Penem and carbapenem compounds having a group of formula --SA' are prepared from a corresponding compound having a substituted thio, sulfinyl or sulfonyl group at this position by reaction with a compound A'SH (where A' is an organic group) in the presence of a salt of a metal of Group II or III of the Periodic Table.

  化合物的化学式（I）：##STR1##其中：R.sup.1是氢或羟基保护基；R.sup.2是烷基，烷氧基，卤素，可选择取代的苯基或可选择取代的苯氧基；R.sup.3是可选择取代的吡啶基，可选择取代的喹啉基或带有化学式--CYNR.sup.5 R.sup.6的苯基，其中Y为氧或硫，R.sup.5和R.sup.6分别为烷基，芳基或芳基烷基，或R.sup.5和R.sup.6以及它们连接的氮共同形成杂环基；R.sup.4为氢或氨基保护基；Z为硫或氧；在头孢内酯类化合物的制备中是有价值的中间体，并在转化为这类头孢内酯类化合物时保持理想的构型。具有化学式--SA'的头孢内酯和头孢内酯类化合物是通过将在该位置具有取代硫，亚硫酰基或磺酰基团的相应化合物与存在于周期表第II或III族金属盐的存在下与化合物A'SH（其中A'为有机基）反应制备的。
• Metal catalyzed displacement process
  申请人：Sankyo Company, Limited

  公开号：US05681951A1

  公开（公告）日：1997-10-28

  A process for preparing a compound of formula (I'): ##STR1## comprising reacting a compound of formula (II'): ##STR2## with a compound of formula (III'): A'SH (III') wherein the reaction of the compound of formula (II') and the compound of formula (III') are carried out in the presence of a salt of a metal of Group II or III of the Periodic Table of Elements, wherein A' is an alkyl, aryl, aralkyl or heterocyclic, R.sup.1' is hydrogen or a carboxy protecting group, R.sup.2' and R.sup.3' can be hydrogen or alkyl, X' can be sulfur, k' is 1 or 2 and R.sup.4' is alkyl, alkenyl, aryl, aralkyl, cycloalkyl or heterocyclic.

  一种制备式（I'）化合物的方法： ##STR1## 包括将式（II'）化合物与式（III'）化合物反应： ##STR2## 其中化合物（II'）和化合物（III'）的反应在元素周期表II或III族金属的盐的存在下进行，其中A'是烷基，芳基，芳烷基或杂环基，R.sup.1'是氢或羧基保护基，R.sup.2'和R.sup.3'可以是氢或烷基，X'可以是硫，k'为1或2，R.sup.4'是烷基，烯基，芳基，芳烷基，环烷基或杂环基。
• Carbapenem derivatives, their preparation and their use as antibiotics
  申请人：Sankyo Company,. Limited

  公开号：US05712267A1

  公开（公告）日：1998-01-27

  Compounds of formula (I): ##STR1## wherein R.sup.1x is hydrogen or methyl, R.sup.2x is hydrogen optionally substituted aliphatic hydrocarbon or acylimidoyl, R.sup.3x is hydrogen or an ester group, and Q.sup.x is cyclic or acyclic nitrogen-containing group. The compounds are potent antibiotics which are resistant to dehydropeptidase I, and are thus useful for the treatment of many microbial infections.

  式(I)的化合物：##STR1## 其中R.sup.1x为氢或甲基，R.sup.2x为氢或可选择的取代脂肪烃基或酰基亚咪唑基，R.sup.3x为氢或酯基，Q.sup.x为环状或非环状含氮基团。这些化合物是强效的抗生素，对去氢肽酶I具有抗性，因此可用于治疗许多微生物感染。
• Silyl enol ether alkylation process
  申请人：Sankyo Company, Limited

  公开号：US05719275A1

  公开（公告）日：1998-02-17

  A method for preparing compounds of formula (I): ##STR1## wherein: R.sup.1 is hydrogen or a hydroxy-protecting group; R.sup.2 is alkyl, alkoxy, halogen, optionally substituted phenyl or optionally substituted phenoxy; R.sup.3 is optionally substituted pyridyl, optionally substituted quinolyl or phenyl group which has a substituent of formula --CYNR.sup.5 R.sup.6, where Y is oxygen or sulfur, and R.sup.5 and R.sup.6 are each alkyl, aryl or aralkyl, or R.sup.5 and R.sup.6 and the nitrogen to which they are attached together form a heterocyclic group; R.sup.4 is hydrogen or an amino-protecting group; and Z is sulfur or oxygen. The process comprises reacting a compound of formula (II): ##STR2## in which R.sup.8, R.sup.9 and R.sup.10 are the same or different and each represents an alkyl group having from 1 to 4 carbon atoms or a phenyl group, with a compound of formula (III): ##STR3## in which R.sup.11 represents an acyloxy, alkylsulfonyl, arylsulfonyl, alkylsulfinyl or arylsulfinyl group.

  一种制备式（I）化合物的方法：其中：R.sup.1是氢或羟基保护基；R.sup.2是烷基，烷氧基，卤素，可选地取代的苯基或可选地取代的苯氧基；R.sup.3是可选地取代的吡啶基，可选地取代的喹啉基或具有式--CYNR.sup.5 R.sup.6的取代基的苯基，其中Y是氧或硫，R.sup.5和R.sup.6分别是烷基，芳基或芳烷基，或R.sup.5和R.sup.6和它们所连接的氮共同形成一个杂环基；R.sup.4是氢或氨基保护基；Z是硫或氧。该过程包括将式（II）的化合物与式（III）的化合物反应：其中R.sup.8，R.sup.9和R.sup.10相同或不同，每个代表具有1至4个碳原子的烷基或苯基。其中，式（II）为：##STR2##式（III）为：##STR3##
• Process for preparing carbapenem and penem compounds and new compounds involved in that process
  申请人：SANKYO COMPANY LIMITED

  公开号：EP0587436B1

  公开（公告）日：2000-05-10