(1'S,2'R,3'S,4'S)-1-<2,3-dihydroxy-4-(hydroxymethyl)cyclopentan-1-yl>thymine

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: (1'S,2'R,3'S,4'S)-1-<2,3-dihydroxy-4-(hydroxymethyl)cyclopentan-1-yl>thymine
• 英文别名: L-carba-ribothymidine；1-[(1S,2R,3S,4S)-2,3-dihydroxy-4-(hydroxymethyl)cyclopentyl]-5-methyl-pyrimidine-2,4-dione；1-[(1S,2R,3S,4S)-2,3-dihydroxy-4-(hydroxymethyl)cyclopentyl]-5-methylpyrimidine-2,4-dione
• 化学式: C₁₁H₁₆N₂O₅
• 分子量: 256.258
• InChiKey: OHFMYSNQKZBRNM-XSPKLOCKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  110
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (+/-)-2,2-dimethyl-3αβ,6αβ-dihydro-4H-cyclopenta-1,3-dioxol-4-one 在 palladium on activated charcoal ammonium hydroxide 、 叠氮化锂 、 甲基叔丁基醚 、 水 、 氢气 、 二异丁基氢化铝 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， -78.0~140.0 ℃ 、137.9 kPa 条件下， 反应 33.5h， 生成 (1'S,2'R,3'S,4'S)-1-<2,3-dihydroxy-4-(hydroxymethyl)cyclopentan-1-yl>thymine
  参考文献：
  名称：

  Asymmetric synthesis of L-cyclopentyl carbocyclic nucleosides

  摘要：

  Asymmetric synthesis of L-carbocyclic nucleosides, (+)-beta-L-aristeromycin (11) and its thymine analog (12) was accomplished. The key intermediate 3 was synthesized by a regioselective conjugate addition to the enone 1 followed by DIBAL-H reduction. Coupling of 4 with heterocycle or construction of heterocyle by a linear approach gave 11 and 12. This is the first asymmetric synthesis of L-cyclopentyl carbocyclic nucleosides. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00898-8

文献信息

• Synthesis of 2′,3′-Modified Carbocyclic L-Nucleoside Analogues
  作者：Sönke Jessel、Chris Meier

  DOI：10.1002/ejoc.201001473

  日期：2011.3

  New divergent approaches to 2',3'-modified carbocyclic L -nucleoside analogues starting from enantiomerically pure (1R,2S)- or (1S,2R)-2-(benzyloxymethyl)cyclopent-3-enol are described. In the key step, stereochemically pure cyclopentanols were condensed with N3-protected thymine through a modified Mitsunobu protocol. Moreover, several routes to different cyclopentanol derivatives, to prepare carbocyclic

  描述了从对映体纯 (1R,2S)-或 (1S,2R)-2-(苄氧基甲基)cyclopent-3-enol 开始的 2',3'-修饰的碳环 L-核苷类似物的新发散方法。在关键步骤中，立体化学纯环戊醇通过改进的 Mitsunobu 协议与 N3 保护的胸腺嘧啶缩合。此外，通过不同的环戊醇衍生物，制备碳环L -2',3'-didehydro-2',3'-dideoxynucleosides (L -d4N), L -2',3'-dideoxynucleosides (L -ddN),和L-核糖核苷被报道。
• Asymmetric synthesis of L-cyclopentyl carbocyclic nucleosides
  作者：Peiyuan Wang、Luigi A. Agrofoglio、M. Gary Newton、Chung K. Chu

  DOI：10.1016/s0040-4039(97)00898-8

  日期：1997.6

  Asymmetric synthesis of L-carbocyclic nucleosides, (+)-beta-L-aristeromycin (11) and its thymine analog (12) was accomplished. The key intermediate 3 was synthesized by a regioselective conjugate addition to the enone 1 followed by DIBAL-H reduction. Coupling of 4 with heterocycle or construction of heterocyle by a linear approach gave 11 and 12. This is the first asymmetric synthesis of L-cyclopentyl carbocyclic nucleosides. (C) 1997 Elsevier Science Ltd.
• Chiral Synthesis of Carbocyclic Analogues of <scp>l</scp>-ribofuranosides
  作者：Peiyuan Wang、Luigi A. Agrofoglio、M. Gary Newton、Chung K. Chu

  DOI：10.1021/jo9812330

  日期：1999.5.1