D-6-[6-(2-(N-allyloxycarbonyl)aminoadipyl)]aminopenicillanic acid diallyl ester | 309249-43-2

• 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: D-6-[6-(2-(N-allyloxycarbonyl)aminoadipyl)]aminopenicillanic acid diallyl ester
• 英文别名: prop-2-enyl (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[[(5R)-6-oxo-6-prop-2-enoxy-5-(prop-2-enoxycarbonylamino)hexanoyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• CAS: 309249-43-2
• 化学式: C₂₄H₃₃N₃O₈S
• 分子量: 523.607
• InChiKey: QSMSLWTYBFLCIC-PHXBYCTMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  36
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  166
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  D-6-[6-(2-(N-allyloxycarbonyl)aminoadipyl)]aminopenicillanic acid diallyl ester 在 四(三苯基膦)钯 、 5,5-二甲基-1,3-环己二酮 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以72%的产率得到penicillin N sodium salt
  参考文献：
  名称：

  Synthesis of Penicillin N and Isopenicillin N

  摘要：

  Enantiomeric 2-(N-allyloxycarbonyl)aminoadipic acid 1-allyl esters were obtained from the corresponding 2-(N-trityl)aminoadipic acid diallyl esters following selective hydrolysis of the allyl 6-ester group and subsequent exchange of the trityl group by the allyloxycarbonyl function. The resulting monoacids were used to acylate 6-aminopenicillanic acid allyl ester using a carbodiimide-mediated coupling. The products, the L- and D-isomers of 6-[6-(2-(N-allyloxycarbonyl) aminoadipyl)]aminopenicillanic acid diallyl ester were deprotected in one step by catalytic allyl transfer using tetrakis-(triphenylphosphine)palladium(0) to afford isopenicillin N and penicillin N, respectively. The presented straightforward route to penicillin N and isopenicillin N is uniquely compatible with the sensitive nature of the condensation products and gives entry to a new and high yielding procedure that is superior to existing approaches. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00673-6
• 作为产物：
  描述：

  D-2-(N-trityl)aminoadipic acid diallyl ester 在 盐酸 、 4-二甲氨基吡啶 、 sodium hydroxide 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 水 、 溶剂黄146 、 乙腈 为溶剂， 反应 26.5h， 生成 D-6-[6-(2-(N-allyloxycarbonyl)aminoadipyl)]aminopenicillanic acid diallyl ester
  参考文献：
  名称：

  Synthesis of Penicillin N and Isopenicillin N

  摘要：

  Enantiomeric 2-(N-allyloxycarbonyl)aminoadipic acid 1-allyl esters were obtained from the corresponding 2-(N-trityl)aminoadipic acid diallyl esters following selective hydrolysis of the allyl 6-ester group and subsequent exchange of the trityl group by the allyloxycarbonyl function. The resulting monoacids were used to acylate 6-aminopenicillanic acid allyl ester using a carbodiimide-mediated coupling. The products, the L- and D-isomers of 6-[6-(2-(N-allyloxycarbonyl) aminoadipyl)]aminopenicillanic acid diallyl ester were deprotected in one step by catalytic allyl transfer using tetrakis-(triphenylphosphine)palladium(0) to afford isopenicillin N and penicillin N, respectively. The presented straightforward route to penicillin N and isopenicillin N is uniquely compatible with the sensitive nature of the condensation products and gives entry to a new and high yielding procedure that is superior to existing approaches. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00673-6

文献信息

• Synthesis of Penicillin N and Isopenicillin N
  作者：Rute Madeira Lau、Jacques T.H. van Eupen、Dick Schipper、Godefridus I. Tesser、Jan Verweij、Erik de Vroom

  DOI：10.1016/s0040-4020(00)00673-6

  日期：2000.9

  Enantiomeric 2-(N-allyloxycarbonyl)aminoadipic acid 1-allyl esters were obtained from the corresponding 2-(N-trityl)aminoadipic acid diallyl esters following selective hydrolysis of the allyl 6-ester group and subsequent exchange of the trityl group by the allyloxycarbonyl function. The resulting monoacids were used to acylate 6-aminopenicillanic acid allyl ester using a carbodiimide-mediated coupling. The products, the L- and D-isomers of 6-[6-(2-(N-allyloxycarbonyl) aminoadipyl)]aminopenicillanic acid diallyl ester were deprotected in one step by catalytic allyl transfer using tetrakis-(triphenylphosphine)palladium(0) to afford isopenicillin N and penicillin N, respectively. The presented straightforward route to penicillin N and isopenicillin N is uniquely compatible with the sensitive nature of the condensation products and gives entry to a new and high yielding procedure that is superior to existing approaches. (C) 2000 Elsevier Science Ltd. All rights reserved.