(S)-4-Acetoxy-3-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester | 80903-62-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-4-Acetoxy-3-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester
• 英文别名: Pivaloyloxymethyl 1-acetoxy-2-methylcarbapen-2-em-3-carboxylate；2,2-dimethylpropanoyloxymethyl (5S)-4-acetyloxy-3-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
• CAS: 80903-62-4
• 化学式: C₁₆H₂₁NO₇
• 分子量: 339.345
• InChiKey: UZNDKMMCEBVNKJ-NKUHCKNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  99.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (S)-3-Methyl-4,7-dioxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester 在 4-二甲氨基吡啶 、 tetrabutylammonium borohydride 作用下， 以 二氯甲烷 为溶剂， 生成 (S)-4-Acetoxy-3-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester
  参考文献：
  名称：

  Photochemical transformation of cephalosporins into carbapenems

  摘要：

  DOI：

  10.1021/ja00379a044

文献信息

• Carbapenams and carbapen-2-ems and process therefor
  申请人：Pfizer Inc.

  公开号：US04429128A1

  公开（公告）日：1984-01-31

  Carbapenam-3-carboxylic acids and carbapen-2-em-3-carboxylic acids substituted at the 1-position with an oxo, a hydroxy or an acetoxy group, variously substituted at the 2-position with such groups as methyl, acetoxymethyl, methanesulfonyloxy, alkoxy, alkylthio, aminoalkylthio or amidinoalkylthio and optionally substituted at the 6-position with a hydroxyalkyl group, an acetoxyalkyl group or a conventional penicillin side-chain, pharmaceutically-acceptable salts thereof and various esters thereof wherein the esterifying group is selectively removed in the laboratory, or hydrolyzed under physiological conditions. These compounds are useful either systemically or topically in the treatment of diseases caused by susceptible microorganisms, as animal feed additives for promotion of growth, or in the preservation of biodegradable materials, or as intermediates to compounds having such antibacterial activity. Key to the synthesis of these compounds is the light catalyzed rearrangement of 2-diazo-1-oxoceph-3-em-4-carboxylates to 1-oxocarbapen-2-em-3-carboxylates, a newly discovered reaction determined to be of general applicability.

  在1-位置上以氧、羟基或乙酰氧基基团取代的碳青霉烯-3-羧酸和碳青霉烯-2-烯-3-羧酸，以各种基团在2-位置上取代，如甲基、乙酰氧甲基、甲烷磺酰氧基、烷氧基、烷基硫醇、氨基烷硫醇或酰胺基烷硫醇，并在6-位置上选择性地以羟基烷基、乙酰氧基烷基或传统青霉素侧链取代，其药学上可接受的盐以及各种酯类，其中酯化基团在实验室中被选择性地去除，或在生理条件下水解。这些化合物在治疗由易感微生物引起的疾病中，无论是系统性还是局部性，作为促进生长的动物饲料添加剂，或在生物可降解材料的保护中，或作为具有抗菌活性的化合物的中间体，都是有用的。这些化合物的合成关键在于光催化2-重氮基-1-氧代头孢-3-烯-4-羧酸酯的重排，形成1-氧代碳青霉烯-2-烯-3-羧酸酯，这是一种新发现的反应，被认为具有普适性。
• Photocatalyzed process for producing carbapenams and carbapen-2-ems
  申请人：Pfizer Inc.

  公开号：US04348264A1

  公开（公告）日：1982-09-07

  Carbapenam-3-carboxylic acids and carbapen-2-em-3-carboxylic acids substituted at the 1-position with an oxo, a hydroxy or an acetoxy group, variously substituted at the 2-position with such groups as methyl, acetoxymethyl, methanesulfonyloxy, alkoxy, alkylthio, aminoalkylthio or amidinoalkylthio and optionally substituted at the 6-position with a hydroxyalkyl group, an acetoxyalkyl group or a conventional penicillin side-chain, pharmaceutically-acceptable salts thereof and various esters thereof wherein the esterifying group is selectively removed in the laboratory, or hydrolyzed under physiological conditions. These compounds are useful either systemically or topically in the treatment of diseases caused by susceptible microorganisms, as animal feed additives for promotion of growth, or in the preservation of biodegradable materials, or as intermediates to compounds having such antibacterial activity. Key to the synthesis of these compounds is the light catalyzed rearrangement of 2-diazo-1-oxoceph-3-em-4-carboxylates to 1-oxocarbapen-2-em-3-carboxylates, a newly discovered reaction determined to be of general applicability.

  在1位取代有氧、羟基或乙酰氧基的碳青霉烯-3-羧酸和碳青霉烯-2-烯-3-羧酸，2位取代有甲基、乙酰氧甲基、甲磺酰氧基、烷氧基、烷基硫基、氨基烷基硫基或酰胺基烷基硫基等基团，6位可选地取代有羟基烷基、乙酰氧基烷基或传统的青霉素侧链，其药学上可接受的盐和各种酯类，其中酯化基团在实验室中被选择性地去除，或在生理条件下水解。这些化合物在治疗由易感微生物引起的疾病、作为动物饲料添加剂促进生长、在生物可降解材料的保护中或作为具有抗菌活性的化合物的中间体中，可以系统或局部使用。这些化合物的合成关键在于光催化的2-重氮-1-氧代头孢-3-烯-4-羧酸酯重排到1-氧代碳青霉烯-2-烯-3-羧酸酯，这是一种新发现的反应，被确定为具有普遍适用性。