(1R,5S,6S)-6-[(R)-1-(tert-butyldimethylsilanyloxyl)ethyl]-2-[[(2R,3R)-2-[[[(S)-2-(4-nitrobenzyloxycarbonyl)amino-3-methyl-1-oxobutyl]amino]methyl]tetrahydro-3-furanyl]thio]-1-methylcarbapen-2-em-3-carboxylic acid 4-nitrobenzyl ester | 357341-55-0

• 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: (1R,5S,6S)-6-[(R)-1-(tert-butyldimethylsilanyloxyl)ethyl]-2-[[(2R,3R)-2-[[[(S)-2-(4-nitrobenzyloxycarbonyl)amino-3-methyl-1-oxobutyl]amino]methyl]tetrahydro-3-furanyl]thio]-1-methylcarbapen-2-em-3-carboxylic acid 4-nitrobenzyl ester
• 英文别名: (4-nitrophenyl)methyl (4R,5S,6S)-6-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-methyl-3-[(2R,3R)-2-[[[(2S)-3-methyl-2-[(4-nitrophenyl)methoxycarbonylamino]butanoyl]amino]methyl]oxolan-3-yl]sulfanyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
• CAS: 357341-55-0
• 化学式: C₄₁H₅₅N₅O₁₂SSi
• 分子量: 870.066
• InChiKey: LPSHNEVGARWEOI-OLSCRHDASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  60
• 可旋转键数：
  18
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  249
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  (1R,5S,6S)-6-[(R)-1-(tert-butyldimethylsilanyloxyl)ethyl]-2-[[(2R,3R)-2-[[[(S)-2-(4-nitrobenzyloxycarbonyl)amino-3-methyl-1-oxobutyl]amino]methyl]tetrahydro-3-furanyl]thio]-1-methylcarbapen-2-em-3-carboxylic acid 4-nitrobenzyl ester 在 ammonium bifluoride 作用下， 以 N-甲基吡咯烷酮 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以82.4%的产率得到[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：

  2,5-anhydro-1-[[[(4-nitrophenyl)methoxy]carbonyl]-L-valyl]amino-1,4-dideoxy-3-thio-D-threo-pentitol 在 4-二甲氨基吡啶 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 亚磷酸三乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 71.0h， 生成 (1R,5S,6S)-6-[(R)-1-(tert-butyldimethylsilanyloxyl)ethyl]-2-[[(2R,3R)-2-[[[(S)-2-(4-nitrobenzyloxycarbonyl)amino-3-methyl-1-oxobutyl]amino]methyl]tetrahydro-3-furanyl]thio]-1-methylcarbapen-2-em-3-carboxylic acid 4-nitrobenzyl ester
  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.