(S)-[1-[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl-2-methylpropyl]carbamic acid (4-nitrophenyl)methyl ester | 161855-96-5

• 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)-[1-[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl-2-methylpropyl]carbamic acid (4-nitrophenyl)methyl ester
• 英文别名: (S)-[[1-(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl-2-methylpropyl]carbamic acid (4-nitrophenyl)methyl ester；p-nitro-carbobenzyloxy-L-valine-N-hydroxysuccinimide ester；(2,5-dioxopyrrolidin-1-yl) (2S)-3-methyl-2-[(4-nitrophenyl)methoxycarbonylamino]butanoate
• CAS: 161855-96-5
• 化学式: C₁₇H₁₉N₃O₈
• 分子量: 393.353
• InChiKey: RBAPOGKCWABDSO-HNNXBMFYSA-N

物化性质

• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  148
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (S)-[1-[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl-2-methylpropyl]carbamic acid (4-nitrophenyl)methyl ester 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 6.0h， 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：

  口服THF1β-甲基卡巴培南的聚合合成。

  摘要：

  从M2-磷酸酯1开始开发了口服THF1β-甲基卡巴培南4（OCA-983）和5的聚合合成方法。M2-磷酸酯1与含有必需的前药侧链9和10的THF硫醇反应，分别以46％和42％的总收率得到所需的口服THF1β-甲基咔ap烯4和5。

  DOI：

  10.7164/antibiotics.52.643
• 作为产物：
  描述：

  L-缬氨酸 在 TEA 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 生成 (S)-[1-[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl-2-methylpropyl]carbamic acid (4-nitrophenyl)methyl ester
  参考文献：
  名称：

  Peptidic prodrugs of novel aminomethyl-THF 1β-methylcarbapenems

  摘要：

  Peptidic prodrugs of the five most active aminomethyl-THF 1 beta-methylcarbapenems were synthesized. Of these, only L-amino acid derivatives from la demonstrated an improved oral activity. These results indicate that the L-amino acid derivatives from la are orally absorbed most likely through the dipeptide and tripeptide transport mechanism. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00281-3

文献信息

• Convergent Syntheses of Oral THF 1.BETA.-Methylcarbapenems.
  作者：PANAYOTA BITHA、ZHONG LI、YANG-I LIN

  DOI：10.7164/antibiotics.52.643

  日期：——

  Convergent syntheses of oral THF 1beta-methylcarbapenems 4 (OCA-983) and 5 starting from M2-phosphate 1 were developed. Reaction of the M2-phosphate 1 with THF thiols containing a requisite prodrug side chain, 9 and 10, gave the desired oral THF 1beta-methylcarbapenems 4 and 5, respectively, in 46% and 42% overall yields.

  从M2-磷酸酯1开始开发了口服THF1β-甲基卡巴培南4（OCA-983）和5的聚合合成方法。M2-磷酸酯1与含有必需的前药侧链9和10的THF硫醇反应，分别以46％和42％的总收率得到所需的口服THF1β-甲基咔ap烯4和5。
• Peptidic prodrugs of novel aminomethyl-THF 1β-methylcarbapenems
  作者：Yang-I Lin、Panayota Bitha、Subas M. Sakya、Zhong Li、Stanley A. Lang、Youjun Yang、Niraja Bhachech、William J. Weiss、Peter J. Petersen、Nilda V. Jacobus、Karen Bush、Raymond T. Testa

  DOI：10.1016/s0960-894x(97)00281-3

  日期：1997.7

  Peptidic prodrugs of the five most active aminomethyl-THF 1 beta-methylcarbapenems were synthesized. Of these, only L-amino acid derivatives from la demonstrated an improved oral activity. These results indicate that the L-amino acid derivatives from la are orally absorbed most likely through the dipeptide and tripeptide transport mechanism. (C) 1997 Elsevier Science Ltd.
• 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.