(1S,3S,5R,6R,8R)-5-hydroxy-6-hydroxymethyl-3-(N-[4-pyren-1-ylbutanoyl]piperazino)methyl-8-(thymin-1-yl)-2,7-dioxabicyclo[3.3.0]octane | 866934-32-9

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: (1S,3S,5R,6R,8R)-5-hydroxy-6-hydroxymethyl-3-(N-[4-pyren-1-ylbutanoyl]piperazino)methyl-8-(thymin-1-yl)-2,7-dioxabicyclo[3.3.0]octane
• CAS: 866934-32-9
• 化学式: C₃₇H₄₀N₄O₇
• 分子量: 652.747
• InChiKey: AZMMRKLGYYTFBC-DUWJBPDTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.69
• 重原子数：
  48.0
• 可旋转键数：
  8.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  137.33
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (1S,3S,5R,6R,8R)-5-hydroxy-6-hydroxymethyl-3-(N-[4-pyren-1-ylbutanoyl]piperazino)methyl-8-(thymin-1-yl)-2,7-dioxabicyclo[3.3.0]octane 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 1.5h， 生成 (1S,3S,5R,6R,8R)-5-(2-cyanoethoxy(diisopropylamino)phosphinoxy)-6-((4,4'-dimethoxytrityl)oxymethyl)-3-(N-[4-pyren-1-ylbutanoyl]piperazino)methyl-8-(thymin-1-yl)-2,7-dioxabicyclo[3.3.0]octane
  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：

  (1S,5R,6R,8R)-5-hydroxy-6-hydroxymethyl-3-piperazinomethyl-8-(thymin-1-yl)-2,7-dioxabicyclo[3.3.0]octane 、 1-芘丁酸 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以49%的产率得到(1S,3R,5R,6R,8R)-5-hydroxy-6-hydroxymethyl-3-(N-[4-pyren-1-ylbutanoyl]piperazino)methyl-8-(thymin-1-yl)-2,7-dioxabicyclo[3.3.0]octane
  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