1(R)-(N⁹-Adenyl)-4(S)-cyclopent-2-ene | 172323-67-0

• 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: 1(R)-(N⁹-Adenyl)-4(S)-cyclopent-2-ene
• 英文别名: tert-butyl N-[(2S)-1-[[(1S,4R)-4-(6-aminopurin-9-yl)cyclopent-2-en-1-yl]amino]-1-oxopropan-2-yl]carbamate
• CAS: 172323-67-0
• 化学式: C₁₈H₂₅N₇O₃
• 分子量: 387.442
• InChiKey: BJRWUMQSHPVQRI-TUAOUCFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  137
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1(R)-(N⁹-Adenyl)-4(S)-cyclopent-2-ene 在 四氧化锇 、 N-甲基吗啉氧化物 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 叔丁醇 为溶剂， 反应 3.5h， 生成 L-alanylcarbocyclic aristeromycin
  参考文献：
  名称：

  Synthesis of enantiomerically pure 5'-aza-noraristeromycin analogs

  摘要：

  The synthesis of a novel class of enantiomerically pure azanoraristeromycins is described. An asymmetric hetero Diels-Alder reaction using amino acid-derived chiral acylnitroso dienophiles 2 was used to prepare optically pure allylic acetate substrate 10. The palladium(0)-catalyzed addition of the sodium salt of adenine to optically pure acetate 10 was achieved to give N-9-alkylated adenine adduct 11 in good yield. Catalytic osmium tetraoxide dihydroxylation of the didehydro analog provided both diol products 17 and 18, corresponding to common natural and unnatural nucleosides, respectively.

  DOI：

  10.1021/jo00123a015
• 作为产物：
  描述：

  cis-(1R,3S)-3-<(N-Boc-L-alanyl)amino>cyclopent-4-enol 在 四(三苯基膦)钯 吡啶 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.17h， 生成 1(R)-(N⁹-Adenyl)-4(S)-cyclopent-2-ene
  参考文献：
  名称：

  Synthesis of enantiomerically pure 5'-aza-noraristeromycin analogs

  摘要：

  The synthesis of a novel class of enantiomerically pure azanoraristeromycins is described. An asymmetric hetero Diels-Alder reaction using amino acid-derived chiral acylnitroso dienophiles 2 was used to prepare optically pure allylic acetate substrate 10. The palladium(0)-catalyzed addition of the sodium salt of adenine to optically pure acetate 10 was achieved to give N-9-alkylated adenine adduct 11 in good yield. Catalytic osmium tetraoxide dihydroxylation of the didehydro analog provided both diol products 17 and 18, corresponding to common natural and unnatural nucleosides, respectively.

  DOI：

  10.1021/jo00123a015

文献信息

• Synthesis of enantiomerically pure 5'-aza-noraristeromycin analogs
  作者：Arun Ghosh、Allen R. Ritter、Marvin J. Miller

  DOI：10.1021/jo00123a015

  日期：1995.9

  The synthesis of a novel class of enantiomerically pure azanoraristeromycins is described. An asymmetric hetero Diels-Alder reaction using amino acid-derived chiral acylnitroso dienophiles 2 was used to prepare optically pure allylic acetate substrate 10. The palladium(0)-catalyzed addition of the sodium salt of adenine to optically pure acetate 10 was achieved to give N-9-alkylated adenine adduct 11 in good yield. Catalytic osmium tetraoxide dihydroxylation of the didehydro analog provided both diol products 17 and 18, corresponding to common natural and unnatural nucleosides, respectively.