Benzoic acid (1S,2R,3S,5S)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-cyclopentyl ester | 179761-48-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: Benzoic acid (1S,2R,3S,5S)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-cyclopentyl ester
• CAS: 179761-48-9
• 化学式: C₃₉H₃₈N₂O₈
• 分子量: 662.739
• InChiKey: LKVBISJUCRSJKL-KWRMZWAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.02
• 重原子数：
  49.0
• 可旋转键数：
  11.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  129.08
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  双(二异丙基氨基)(2-氰基乙氧基)膦 、 Benzoic acid (1S,2R,3S,5S)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-cyclopentyl ester 在 (i-C₃H₇)2NH₂⁺CHN₄ 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以97%的产率得到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：

  Benzoic acid (1S,2R,3S,5S)-3-benzyloxy-2-benzyloxymethyl-5-[3-((Z)-3-methoxy-2-methyl-acryloyl)-ureido]-cyclopentyl ester 在 palladium on activated charcoal 盐酸 、 4-二甲氨基吡啶 、 氢气 、 三乙胺 作用下， 以 吡啶 、 甲醇 、 乙醇 、 水 、 乙酸乙酯 为溶剂， 反应 30.0h， 生成 Benzoic acid (1S,2R,3S,5S)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-hydroxy-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