Benzoic acid (1S,2R,3S,5S)-3-hydroxy-2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-cyclopentyl ester | 169235-69-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Benzoic acid (1S,2R,3S,5S)-3-hydroxy-2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-cyclopentyl ester
• CAS: 169235-69-2
• 化学式: C₁₈H₂₀N₂O₆
• 分子量: 360.367
• InChiKey: QFGFNMKNEYGGLD-QPSCCSFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.02
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  121.62
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Benzoic acid (1S,2R,3S,5S)-3-hydroxy-2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-cyclopentyl ester 在 4-二甲氨基吡啶 、 (i-C₃H₇)2NH₂⁺CHN₄ 、 三乙胺 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 Benzoic acid (1S,2S,3S,5S)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-[(2-cyano-ethoxy)-diisopropylamino-phosphanyloxy]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-cyclopentyl ester
  参考文献：
  名称：

  Crystal Structures of Oligodeoxyribonucleotides Containing 6‘-α-Methyl and 6‘-α-Hydroxy Carbocyclic Thymidines

  摘要：

  The X-ray crystal structures of two self-complementary DNA duplexes with the sequence d(CGCGAAt(Me/OH)t(Me/OH)CGCG) containing four 6'-alpha-methyl (t(Me)) or four 6'-alpha-hydroxy carbocyclic thymidines (t(OH)), respectively, have been determined. Both structures are isomorphous to the native Dickerson-Drew dodecamer duplex [d(CGCGAATTCGCG)](2). The cyclopentane moieties of the modified carbocyclic thymidine residues lacking the deoxyribose 4'-oxygen adopt either C2'-endo or C1'-exo B-DNA type puckers. The dodecamer duplex incorporating 6'-alpha-methyl carbocyclic thymidines shows an enlarged minor groove relative to both the unmodified duplex and the one with incorporated 6'-alpha-hydroxy carbocyclic thymidines. The pairing of oligonucleotides containing single or multiple 6'-alpha-substituted carbocyclic thymidines with complementary DNA is discussed on the basis of the structural data.

  DOI：

  10.1021/ja962406a
• 作为产物：
  描述：

  (1S,2S,3S,5S)-5-azido-3-(benzyloxy)-2-(benzyloxymethyl)cyclopentanol 在 palladium on activated charcoal 、 Lindlar's catalyst 盐酸 、 氢气 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 52.5h， 生成 Benzoic acid (1S,2R,3S,5S)-3-hydroxy-2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-cyclopentyl ester
  参考文献：
  名称：

  Crystal Structures of Oligodeoxyribonucleotides Containing 6‘-α-Methyl and 6‘-α-Hydroxy Carbocyclic Thymidines

  摘要：

  The X-ray crystal structures of two self-complementary DNA duplexes with the sequence d(CGCGAAt(Me/OH)t(Me/OH)CGCG) containing four 6'-alpha-methyl (t(Me)) or four 6'-alpha-hydroxy carbocyclic thymidines (t(OH)), respectively, have been determined. Both structures are isomorphous to the native Dickerson-Drew dodecamer duplex [d(CGCGAATTCGCG)](2). The cyclopentane moieties of the modified carbocyclic thymidine residues lacking the deoxyribose 4'-oxygen adopt either C2'-endo or C1'-exo B-DNA type puckers. The dodecamer duplex incorporating 6'-alpha-methyl carbocyclic thymidines shows an enlarged minor groove relative to both the unmodified duplex and the one with incorporated 6'-alpha-hydroxy carbocyclic thymidines. The pairing of oligonucleotides containing single or multiple 6'-alpha-substituted carbocyclic thymidines with complementary DNA is discussed on the basis of the structural data.

  DOI：

  10.1021/ja962406a