(+)-(5R,6S)-6-[(R)-1-hydroxyethyl]-3-(pyridin-3-yl)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester

• 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: (+)-(5R,6S)-6-[(R)-1-hydroxyethyl]-3-(pyridin-3-yl)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester
• 英文别名: allyl (+)-(5R,6S)-6-[(R)-1-hydroxyethyl]-3-(pyridin-3-yl)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate；allyl (5R,6S)-6-[(R)-1-hydroxyethyl]-7-oxo-3-(3-pyridyl)-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate；allyl (5R,6S)-6-[(R)-1-hydroxyethyl]-7-oxo-3-(pyridin-3-yl)-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate；(+)-(5R,6S)-6-[(R)-1-hydroxyethyl]-3-(3-pyridyl)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester；allyl (+)-(5R,6S)-6-[(R)-1-hydroxyethyl]-3-(3-pyridyl)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate；(+)-(5R, 6S)-6-[(R)-1-hydroxyethyl]-3-(3-pyridyl)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester；prop-2-enyl (5R,6S)-6-[(1R)-1-hydroxyethyl]-7-oxo-3-pyridin-3-yl-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
• 化学式: C₁₆H₁₆N₂O₄S
• 分子量: 332.38
• InChiKey: ZDUXHUYLQMZMIK-BPYAMOTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+)-(5R,6S)-6-[(R)-1-hydroxyethyl]-3-(pyridin-3-yl)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester 生成 4-Thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 6-[(1R)-1-hydroxyethyl]-7-oxo-3-(3-pyridinyl)-, (5R,6S)-
  参考文献：
  名称：

  J. Antibiot. 1990, 43, 306-313

  摘要：

  DOI：
• 作为产物：
  描述：

  prop-2-enyl 2-[(3S,4R)-3-[(1R)-1-hydroxyethyl]-2-oxo-4-(pyridine-3-carbonylsulfanyl)azetidin-1-yl]-2-(triphenyl-λ5-phosphanylidene)acetate 生成 (+)-(5R,6S)-6-[(R)-1-hydroxyethyl]-3-(pyridin-3-yl)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester
  参考文献：
  名称：

  J. Antibiot. 1990, 43, 306-313

  摘要：

  DOI：

文献信息

• Crystalline esters of (+)-(5R,
  申请人：Takeda Chemical Industries Ltd.

  公开号：US05492903A1

  公开（公告）日：1996-02-20

  Crystalline acetoxymethyl and pivaloyloxymethyl esters of (+)-(5R, 6S)-6-[(R)-1-hydroxyethyl]-3-(3-pyridyl)-7-oxo-4-thia-1-azabicyclo-[3.2.0] hept-2-ene-carboxylic acid can be obtained by adding a poor solvent to a solution of acetoxymethyl or pivaloyloxymethyl ester of (+)-(5R, 6S)-6-[(R)-1-hydroxyethyl]-3-(3-pyridyl)-7-oxo-4-thia-1-azabicyclo-[3.2.0] hept-2-ene-carboxylic acid in a good solvent. The crystalline penem compounds obtained show improved stability and are useful antibacterial agents.

  (+)-(5R, 6S)-6-[(R)-1-羟乙基]-3-(3-吡啶基)-7-氧代-4-硫-1-氮杂双环[3.2.0]庚-2-烯-羧酸的结晶乙酰氧甲基和皮瓦洛氧甲基酯可以通过向良溶剂中加入乙酰氧甲基或皮瓦洛氧甲基酯的溶液来获得。获得的结晶青霉素类化合物表现出改善的稳定性，并可用作抗菌剂。
• Crystalline penem, its production and use
  申请人：TAKEDA CHEMICAL INDUSTRIES, LTD.

  公开号：EP0499274A1

  公开（公告）日：1992-08-19

  A process for producing crystalline acetoxymethyl ester of (+)-(5R,6S)-6- [(R)-1-hydroxyethyl]-3-(3-pyridyl)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid by adding a poor solvent to a solution of acetoxymethyl ester of (+)-(5R,6S)-6-[(R)-1-hydroxyethyl]-3-(3-pyridyl)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid in a good solvent is disclosed. The crystalline penem compound is useful as an antibacterial agent.

  揭示了一种通过向良溶剂中的(+)-(5R,6S)-6-[(R)-1-羟乙基]-3-(3-吡啶基)-7-氧代-4-硫代-1-氮杂双环[3.2.0]庚-2-烯-2-羧酸的乙酰氧甲基酯溶液中添加贫溶剂来生产结晶乙酰氧甲基酯的过程。这种结晶的青霉素类化合物可用作抗菌剂。
• BEDESCHI, A.;VISENTIN, G.;PERRONE, E.;GIUDICI, F.;ZARINI, F.;FRANCESCHI, +, J. ANTIBIOTICS, 43,(1990) N, C. 306-313
  作者：BEDESCHI, A.、VISENTIN, G.、PERRONE, E.、GIUDICI, F.、ZARINI, F.、FRANCESCHI, +

  DOI：——

  日期：——