(2R,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-carbaldehyde | 139888-01-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: (2R,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-carbaldehyde
• 英文别名: 3'-O-t-butyldimethylsilyl-4'-formylthymidine；(2R,3S,5R)-3-[tert-butyl(dimethyl)silyl]oxy-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolane-2-carbaldehyde
• CAS: 139888-01-0
• 化学式: C₁₇H₂₈N₂O₆Si
• 分子量: 384.505
• InChiKey: LMJPESOUMPFNND-OGHNNQOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.08
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-carbaldehyde 在 sodium perborate 、 二甲基硫 、 硼烷 、 sodium hydride 、 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 生成 1-[(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-((E)-7-hydroxy-hept-1-enyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Oligodeoxynucleotide probes with multiple labels linked to the 4′-position of thymidine monomers: Excellent duplex stability and detection sensitivity

  摘要：

  A modified thymidine phosphoramidite monomer 1 has been synthesized bearing a 4'-linker arm terminating in a protected primary amine. This monomer has been incorporated once, three and four times, respectively, into short oligodeoxynucleotide probes targeting a specific sequence in the genome of Mycobacterium tuberculosis. These probes, following standard biotinylation, retained their ability to form hybrid duplex DNA structures and the two multiply labeled probes provided a stronger detection signal than the mono biotinylated probe.

  DOI：

  10.1016/s0040-4039(00)78243-8
• 作为产物：
  描述：

  3'-O-(tert-butyldimethylsilyl)-4'-(hydroxymethyl)-thymidine 在 草酸氯化物 、 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 生成 (2R,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-carbaldehyde
  参考文献：
  名称：

  Oligodeoxynucleotide probes with multiple labels linked to the 4′-position of thymidine monomers: Excellent duplex stability and detection sensitivity

  摘要：

  A modified thymidine phosphoramidite monomer 1 has been synthesized bearing a 4'-linker arm terminating in a protected primary amine. This monomer has been incorporated once, three and four times, respectively, into short oligodeoxynucleotide probes targeting a specific sequence in the genome of Mycobacterium tuberculosis. These probes, following standard biotinylation, retained their ability to form hybrid duplex DNA structures and the two multiply labeled probes provided a stronger detection signal than the mono biotinylated probe.

  DOI：

  10.1016/s0040-4039(00)78243-8

文献信息

• 4'-substituted nucleosides
  申请人：Syntex (U.S.A.) Inc.

  公开号：US05192749A1

  公开（公告）日：1993-03-09

  Nucleosides compounds of Formula I: ##STR1## wherein B is a purine or a pyrimidine; X and X' are H; Y is H; Y' is OH, F or H; or Y' and X' together makes a bond; Z is ##STR2## where n is zero, one, two or three; or Y' and Z together form a cyclic phosphate ester; Z' is --CN, --CH.sub.3, CH.sub.2 N.sub.3 or --CH.sub.2 J, where J is a halogen atom; or Z' and Y' together are --CH.sub.2 O--; and pharmaceutically acceptable esters, ethers, amides, N-acyl moieties and salts thereof.

  化合物I式的核苷：##STR1## 其中B是嘌呤或嘧啶；X和X'是H；Y是H；Y'是OH，F或H；或者Y'和X'一起形成键；Z是##STR2## 其中n为零，一，二或三；或者Y'和Z一起形成环磷酸酯；Z'是--CN，--CH.sub.3，CH.sub.2 N.sub.3或--CH.sub.2 J，其中J是卤素原子；或者Z'和Y'一起是--CH.sub.2 O--；以及其药学上可接受的酯，醚，酰胺，N-酰基基团和盐。
• Bifunctional nucleosides, oligomers thereof, and methods of making and
  申请人：Sanofi

  公开号：US05892024A1

  公开（公告）日：1999-04-06

  Disclosed are novel bifunctional nucleoside analogs and oligonucleosides of 3-4 bases (trimers and tetramers) and longer containing at least two consecutive internucleoside linkages of two carbon-one nitrogen atom or two carbon-one oxygen atom (3'-NCC-5', 3'-CNC-5', 3'-OCC-5') internucleoside linkages. The bifunctional nucleosides are useful for preparing the trimers and tetramers, which, in turn, are useful, together with the nucleosides, in preparing oligonucleosides as well as chimeric oligonucleotide analogs, preferably antisense oligonucleosides and oligonucleotide analogs, of 6 to about 60 bases having at least two consecutive internucleoside linkages of two carbon atoms and one nitrogen atom or 2 carbon atoms and one oxygen atom in the oligonucleoside backbone.

  本发明涉及一种新型的双功能核苷类似物和含有至少两个连续的2碳-1氮原子或2碳-1氧原子（3'-NCC-5'，3'-CNC-5'，3'-OCC-5'）的核苷类似物和3-4个碱基（三聚体和四聚体）及更长的寡核苷酸。这些双功能核苷可用于制备三聚体和四聚体，这些三聚体和四聚体与核苷类似物一起，可用于制备寡核苷酸以及嵌合寡核苷酸类似物，优选为6到约60个碱基的反义寡核苷酸和寡核苷酸类似物，其中至少有两个连续的2碳原子和1氮原子或2碳原子和1氧原子的间核苷酸连接。