S-[(2R,3R)-tetrahydro-2-[[[(S)-3-methyl-2-[[[(4-nitrophenyl)methoxy]carbonyl]amino]-1-oxobutyl]amino]methyl]-3-furanyl](α,2S,3S)-3-[(R)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-α-methyl-4-oxo-2-azetidinemethanethiolate | 357341-53-8

• 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: S-[(2R,3R)-tetrahydro-2-[[[(S)-3-methyl-2-[[[(4-nitrophenyl)methoxy]carbonyl]amino]-1-oxobutyl]amino]methyl]-3-furanyl](α,2S,3S)-3-[(R)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-α-methyl-4-oxo-2-azetidinemethanethiolate
• 英文别名: S-[(2R,3R)-2-[[[(2S)-3-methyl-2-[(4-nitrophenyl)methoxycarbonylamino]butanoyl]amino]methyl]oxolan-3-yl] (2R)-2-[(2S,3S)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl]propanethioate
• CAS: 357341-53-8
• 化学式: C₃₂H₅₀N₄O₉SSi
• 分子量: 694.922
• InChiKey: KPRZFQRPOZTUJA-PMEKXCSPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.54
• 重原子数：
  47
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  203
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  S-[(2R,3R)-tetrahydro-2-[[[(S)-3-methyl-2-[[[(4-nitrophenyl)methoxy]carbonyl]amino]-1-oxobutyl]amino]methyl]-3-furanyl](α,2S,3S)-3-[(R)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-α-methyl-4-oxo-2-azetidinemethanethiolate 在 ammonium bifluoride 、 三乙胺 、 亚磷酸三乙酯 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 、 N,N-二甲基甲酰胺 为溶剂， 反应 64.0h， 生成 [1(S),3[4R,5S,6S(R)]]-1-[[[[2-(4-nitrophenyl)methoxy]carbonyl]amino-3-methyl-1-oxobutyl]amino]-2,5-anhydro-3-S-[6-(1-hydroxyethyl)-4-methyl-2-[[(4-nitrophenyl)methoxy]carbonyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-en-3-yl]-1,4-dideoxy-3-thio-D-threo-pentitol
  参考文献：
  名称：

  EFFICIENT SYNTHESIS OF ORAL THF 1β-METHYLCARBAPENEM (OCA-983) VIA THE WITTIG PROCESS

  摘要：

  An efficient and reproducible synthesis of orally active 2-tetrahydrofuranylthio-1 beta -methylcarbapenem 16 (OCA-983) via the Wittig process was developed. The intramolecular reductive cyclization of the thioester-oxalimide 13 with triethyl phosphite to the 2-tetrahydrofuranylthio-1 beta -methylcarbapenem 14 was carried out in two steps in order to obtain a reproducible yield.

  DOI：

  10.1081/scc-100000586
• 作为产物：
  描述：

  (S)-[1-[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl-2-methylpropyl]carbamic acid (4-nitrophenyl)methyl ester 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 61.0h， 生成 S-[(2R,3R)-tetrahydro-2-[[[(S)-3-methyl-2-[[[(4-nitrophenyl)methoxy]carbonyl]amino]-1-oxobutyl]amino]methyl]-3-furanyl](α,2S,3S)-3-[(R)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-α-methyl-4-oxo-2-azetidinemethanethiolate
  参考文献：
  名称：

  EFFICIENT SYNTHESIS OF ORAL THF 1β-METHYLCARBAPENEM (OCA-983) VIA THE WITTIG PROCESS

  摘要：

  An efficient and reproducible synthesis of orally active 2-tetrahydrofuranylthio-1 beta -methylcarbapenem 16 (OCA-983) via the Wittig process was developed. The intramolecular reductive cyclization of the thioester-oxalimide 13 with triethyl phosphite to the 2-tetrahydrofuranylthio-1 beta -methylcarbapenem 14 was carried out in two steps in order to obtain a reproducible yield.

  DOI：

  10.1081/scc-100000586

文献信息

• EFFICIENT SYNTHESIS OF ORAL THF 1β-METHYLCARBAPENEM (OCA-983) VIA THE WITTIG PROCESS
  作者：Panayota Bitha、Yang-I Lin

  DOI：10.1081/scc-100000586

  日期：2001.1

  An efficient and reproducible synthesis of orally active 2-tetrahydrofuranylthio-1 beta -methylcarbapenem 16 (OCA-983) via the Wittig process was developed. The intramolecular reductive cyclization of the thioester-oxalimide 13 with triethyl phosphite to the 2-tetrahydrofuranylthio-1 beta -methylcarbapenem 14 was carried out in two steps in order to obtain a reproducible yield.