(-)-1-{(1'R,4'S)-4'-[(R)-methoxycarbonyl(benzyloxycarbonylamino)methyl]cyclopent-2'-enyl}uracil | 725233-47-6

• 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: (-)-1-{(1'R,4'S)-4'-[(R)-methoxycarbonyl(benzyloxycarbonylamino)methyl]cyclopent-2'-enyl}uracil
• 英文别名: methyl (2R)-2-[(1S,4R)-4-(2,4-dioxopyrimidin-1-yl)cyclopent-2-en-1-yl]-2-(phenylmethoxycarbonylamino)acetate
• CAS: 725233-47-6
• 化学式: C₂₀H₂₁N₃O₆
• 分子量: 399.403
• InChiKey: LSNZNXKXUAQWIB-HLLBOEOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (-)-1-{(1'R,4'S)-4'-[(R)-methoxycarbonyl(benzyloxycarbonylamino)methyl]cyclopent-2'-enyl}uracil 在 palladium on activated charcoal lithium hydroxide 、 四氧化锇 、 氢气 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 叔丁醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 生成 (-)-1-{(1'R,2'S,3'R,4'S)-2',3'-dioxy-4'-[(R)-amino(carboxyl)methyl]cyclopentyl}uracil
  参考文献：
  名称：

  Chemoenzymatic Synthesis and Synthetic Application of Enantiopure Aminocyclopentenols:  Total Synthesis of Carbocyclic (+)-Uracil Polyoxin C and Its α-Epimer

  摘要：

  Carbocyclic uracil polyoxin C (+)-2 and its alpha-epimer (-)-3 were synthesized in an efficient fashion from cis-4-(N-tert-butylcarbamoyl)cyclopent-2-en-1-ol (+/-)-7. The synthesis incorporates a concise, inexpensive chemoenzymatic synthesis of enantiopure aminocyclopentenols, a Pd(O)-catalyzed substitution reaction, and a mild reduction of an alpha-nitro ester by TiCl3/sodium borohydride. Significantly, this process demonstrates the synthetic utility of the versatile enantiopure aminocyclopentenol building block 4.

  DOI：

  10.1021/jo0496796
• 作为产物：
  描述：

  (1S,4R)-乙酸-4-叔丁氧羰基氨基-环戊基-2-烯酯 在 盐酸 、 sodium hydroxide palladium diacetate 、 sodium tetrahydroborate 、 titanium(III) chloride 、 L-酒石酸 、 硫酸 、 sodium acetate 、 碳酸氢钠 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 苯 为溶剂， 反应 4.75h， 生成 (-)-1-{(1'R,4'S)-4'-[(R)-methoxycarbonyl(benzyloxycarbonylamino)methyl]cyclopent-2'-enyl}uracil
  参考文献：
  名称：

  Chemoenzymatic Synthesis and Synthetic Application of Enantiopure Aminocyclopentenols:  Total Synthesis of Carbocyclic (+)-Uracil Polyoxin C and Its α-Epimer

  摘要：

  Carbocyclic uracil polyoxin C (+)-2 and its alpha-epimer (-)-3 were synthesized in an efficient fashion from cis-4-(N-tert-butylcarbamoyl)cyclopent-2-en-1-ol (+/-)-7. The synthesis incorporates a concise, inexpensive chemoenzymatic synthesis of enantiopure aminocyclopentenols, a Pd(O)-catalyzed substitution reaction, and a mild reduction of an alpha-nitro ester by TiCl3/sodium borohydride. Significantly, this process demonstrates the synthetic utility of the versatile enantiopure aminocyclopentenol building block 4.

  DOI：

  10.1021/jo0496796

文献信息

• Chemoenzymatic Synthesis and Synthetic Application of Enantiopure Aminocyclopentenols:  Total Synthesis of Carbocyclic (+)-Uracil Polyoxin C and Its α-Epimer
  作者：Fangzheng Li、John B. Brogan、Jennifer L. Gage、Deyi Zhang、Marvin J. Miller

  DOI：10.1021/jo0496796

  日期：2004.6.1

  Carbocyclic uracil polyoxin C (+)-2 and its alpha-epimer (-)-3 were synthesized in an efficient fashion from cis-4-(N-tert-butylcarbamoyl)cyclopent-2-en-1-ol (+/-)-7. The synthesis incorporates a concise, inexpensive chemoenzymatic synthesis of enantiopure aminocyclopentenols, a Pd(O)-catalyzed substitution reaction, and a mild reduction of an alpha-nitro ester by TiCl3/sodium borohydride. Significantly, this process demonstrates the synthetic utility of the versatile enantiopure aminocyclopentenol building block 4.