1-{3,5-Di-O-benzyl-3-C-[(2RS)-2,3-dihydroxypropyl]-β-D-arabinofuranosyl}thymine | 250222-58-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1-{3,5-Di-O-benzyl-3-C-[(2RS)-2,3-dihydroxypropyl]-β-D-arabinofuranosyl}thymine
• 英文别名: 1-[(2R,3S,4S,5R)-4-(2,3-dihydroxypropyl)-3-hydroxy-4-phenylmethoxy-5-(phenylmethoxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 250222-58-3
• 化学式: C₂₇H₃₂N₂O₈
• 分子量: 512.56
• InChiKey: WGZKDMHYKNOLDW-CNSLNGCDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  138
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-{3,5-Di-O-benzyl-3-C-[(2RS)-2,3-dihydroxypropyl]-β-D-arabinofuranosyl}thymine 在 吡啶 、 氨 作用下， 以 甲醇 为溶剂， 反应 25.0h， 生成 Toluene-4-sulfonic acid (3aR,4R,6R,6aS)-3a-benzyloxy-4-benzyloxymethyl-6-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-hexahydro-furo[3,4-b]furan-2-ylmethyl ester
  参考文献：
  名称：

  Oligodeoxynucleotides Containing Diastereomeric O2′,C3′‐linked Bicyclic Nucleotide Units for Functionalization of the Major Groove of Nucleic Acid Duplexes: A Summary and Novel Derivatives*

  摘要：

  The synthesis and evaluation of a range of piperazino-derivatized diastereomeric O2',C3'-linked bicyclic nucleotides are described. A new and optimized protocol is presented for, the synthesis of the bicyclic scaffold on which the piperazino moiety is appended. At low salt concentration, the C2"-S-configured piperazino-modified oligonucleotides display significantly enhanced hybridization affinity toward complementary DNA and RNA targets relative to the unmodified oligonucleotide control, whereas no melting transition is observed for hybrids formed with the C2"-R-configured piperazino-modified oligonucleotides. Upon derivatization of the piperazino moiety with a I-pyrenebutanoyl group, all modified oligonucleotides display strong DNA binding and profound DNA hybridization selectivity.

  DOI：

  10.1081/car-200067044
• 作为产物：
  描述：

  1-(3-C-Allyl-3,5-di-O-benzyl-2-O-methylsulfonyl-β-D-ribofuranosyl)thymine 在 sodium hydroxide 、 四氧化锇 、 N-甲基吲哚酮 、 水 作用下， 以 四氢呋喃 、 乙醇 、 叔丁醇 为溶剂， 反应 22.0h， 生成 1-{3,5-Di-O-benzyl-3-C-[(2RS)-2,3-dihydroxypropyl]-β-D-arabinofuranosyl}thymine
  参考文献：
  名称：

  Raunkjr, Michael; Olsen, Carl E.; Wengel, Jcsper, Journal of the Chemical Society. Perkin transactions I, 1999, # 17, p. 2543 - 2551

  摘要：

  DOI：

文献信息

• Raunkjr, Michael; Olsen, Carl E.; Wengel, Jcsper, Journal of the Chemical Society. Perkin transactions I, 1999, # 17, p. 2543 - 2551
  作者：Raunkjr, Michael、Olsen, Carl E.、Wengel, Jcsper

  DOI：——

  日期：——
• Oligodeoxynucleotides Containing Diastereomeric O2′,C3′‐linked Bicyclic Nucleotide Units for Functionalization of the Major Groove of Nucleic Acid Duplexes: A Summary and Novel Derivatives*
  作者：Michael Raunkjær、Kim Haselmann、Jesper Wengel

  DOI：10.1081/car-200067044

  日期：2005.8.1

  The synthesis and evaluation of a range of piperazino-derivatized diastereomeric O2',C3'-linked bicyclic nucleotides are described. A new and optimized protocol is presented for, the synthesis of the bicyclic scaffold on which the piperazino moiety is appended. At low salt concentration, the C2"-S-configured piperazino-modified oligonucleotides display significantly enhanced hybridization affinity toward complementary DNA and RNA targets relative to the unmodified oligonucleotide control, whereas no melting transition is observed for hybrids formed with the C2"-R-configured piperazino-modified oligonucleotides. Upon derivatization of the piperazino moiety with a I-pyrenebutanoyl group, all modified oligonucleotides display strong DNA binding and profound DNA hybridization selectivity.