Carbonic acid allyl ester (2R,3S,5R)-5-(4-allyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-2-hydroxymethyl-tetrahydro-furan-3-yl ester | 197782-33-5

• 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: Carbonic acid allyl ester (2R,3S,5R)-5-(4-allyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-2-hydroxymethyl-tetrahydro-furan-3-yl ester
• 英文别名: [(2R,3S,5R)-2-(hydroxymethyl)-5-[2-oxo-4-(prop-2-enoxycarbonylamino)pyrimidin-1-yl]oxolan-3-yl] prop-2-enyl carbonate
• CAS: 197782-33-5
• 化学式: C₁₇H₂₁N₃O₈
• 分子量: 395.369
• InChiKey: UUBIMSYWSRYUFA-OUCADQQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  136
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [5'-O-(4,4'-dimethoxytrityl)thymidine-3'-yl]-(N,N'-diisopropyl)methylphosphoramidite 、 Carbonic acid allyl ester (2R,3S,5R)-5-(4-allyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-2-hydroxymethyl-tetrahydro-furan-3-yl ester 在 四氮唑 作用下， 以 乙腈 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  General Synthesis and Binding Affinity of Position-Selective Phosphonodiester- and Phosphotriester-Incorporated Oligodeoxyribonucleotides

  摘要：

  Synthesis of phosphonodiester- and phosphotriester-modified oligodeoxyribonucleotides has been accomplished via the phosphoramidite approach with allylic protection. The modification can be made at the selected position(s) of the oligomers. The efficiency of this method has been demonstrated by the synthesis of base-labile modified oligo(deoxyribonucleotide)s such as the methyl phosphates and phenylphosphonates. Melting temperatures of the duplexes containing these artificial strands indicate that the backbone-alternation, which is made at a single site, does not have a negative influence on the binding affinity to the complementary DNA.

  DOI：

  10.1021/jo00109a024
• 作为产物：
  描述：

  [(2R,3S,5R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-[2-oxo-4-(prop-2-enoxycarbonylamino)pyrimidin-1-yl]oxolan-3-yl] prop-2-enyl carbonate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 Carbonic acid allyl ester (2R,3S,5R)-5-(4-allyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-2-hydroxymethyl-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  General Synthesis and Binding Affinity of Position-Selective Phosphonodiester- and Phosphotriester-Incorporated Oligodeoxyribonucleotides

  摘要：

  Synthesis of phosphonodiester- and phosphotriester-modified oligodeoxyribonucleotides has been accomplished via the phosphoramidite approach with allylic protection. The modification can be made at the selected position(s) of the oligomers. The efficiency of this method has been demonstrated by the synthesis of base-labile modified oligo(deoxyribonucleotide)s such as the methyl phosphates and phenylphosphonates. Melting temperatures of the duplexes containing these artificial strands indicate that the backbone-alternation, which is made at a single site, does not have a negative influence on the binding affinity to the complementary DNA.

  DOI：

  10.1021/jo00109a024

文献信息

• Preparation of Short Oligonucleotides via the Phosphoramidite Method Using a Tetrazole Promoter in a Catalytic Manner
  作者：Yoshihiro Hayakawa、Masanori Kataoka

  DOI：10.1021/ja970685b

  日期：1997.12.1

  (0.05 equiv) in the presence of molecular sieves 13X in acetonitrile (40 °C, 60 min) followed by trimethylsilyl triflate-catalyzed oxidation with bis(trimethylsilyl) peroxide in dichloromethane (40 °C, 10 min). The NPT-catalytic approach is also effective for the synthesis of longer deoxyribonucleotides such as d(5‘CTACCTGT3‘) and 2‘−5‘- or 3‘−5‘-linked ribonucleotides.

  已经开发了一种以催化方式使用四唑促进剂的简便亚磷酰胺方法，用于核苷 3'-亚磷酰胺和核苷的缩合。这种方法对于短寡核苷酸的大规模合成特别有用。例如，通过核苷 3'-N,N-二乙基亚磷酰胺（1.05 当量）和 5'-O-游离核苷（1.00 当量）与 5-( p-硝基苯基)-1H-四唑 (NPT)（0.05 当量）在分子筛存在下 13X 在乙腈中（40 °C，60 分钟），然后在二氯甲烷中用双（三甲基甲硅烷基）过氧化物催化氧化（40 °C，60 分钟） C，10 分钟）。
• General Synthesis and Binding Affinity of Position-Selective Phosphonodiester- and Phosphotriester-Incorporated Oligodeoxyribonucleotides
  作者：Yoshihiro Hayakawa、Masaaki Hirose、Masahiko Hayakawa、Ryoji Noyori

  DOI：10.1021/jo00109a024

  日期：1995.2

  Synthesis of phosphonodiester- and phosphotriester-modified oligodeoxyribonucleotides has been accomplished via the phosphoramidite approach with allylic protection. The modification can be made at the selected position(s) of the oligomers. The efficiency of this method has been demonstrated by the synthesis of base-labile modified oligo(deoxyribonucleotide)s such as the methyl phosphates and phenylphosphonates. Melting temperatures of the duplexes containing these artificial strands indicate that the backbone-alternation, which is made at a single site, does not have a negative influence on the binding affinity to the complementary DNA.