3'-Deoxy-3'-C-(acetoxymethyl)thymidine | 166955-35-7

• 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: 3'-Deoxy-3'-C-(acetoxymethyl)thymidine
• 英文别名: 3'-[(Acetyloxy)methyl]-3'-deoxythymidine；[(2S,3R,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]methyl acetate
• CAS: 166955-35-7
• 化学式: C₁₃H₁₈N₂O₆
• 分子量: 298.296
• InChiKey: BUPCLYOWUNYQRI-GMTAPVOTSA-N

物化性质

• 密度：
  1.311±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  3'-Deoxy-3'-C-(acetoxymethyl)thymidine 在 4-二甲氨基吡啶 、 氨 、 N,N-二异丙基乙胺 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 Diisopropyl-phosphoramidous acid (2S,3R,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-ylmethyl ester 2-cyano-ethyl ester
  参考文献：
  名称：

  Oligodeoxynucleotides with Extended 3'- and 5'-Homologous Internucleotide Linkages.

  摘要：

  3'-Deoxy-3'-C-(hydroxymethyl)thymidine (3'-DHMT) and 5'-deoxy-5'-C-(hydroxymethyl)thymidine (5'-DHMT) have been prepared and used for the synthesis of novel oligodeoxynucleotides containing extended internucleotide linkages. Enzymatic stability toward exonuclease III degradation was studied and hybridization properties were tested, The extended 3'-homologous DNA causes complete cessation of exonuclease III degradation while the extended 5'-homologous DNA shows only same decrease in degradation. Duplexes having extended internucleotide linkages show a minor decrease in hybridization stability. Tripler formation with 20-mer duplexes at pH 5.5 and high salt concentration gave almost no decrease in binding affinity when compared with unmodified tripler formation. UV experiments were also performed with oligodeoxynucleotides containing hairpin structures and bulged bases, Extended linkages in the oligodeoxynucleotides gave a small increase in T-m with sequences containing a loop, but no change or only a small decrease was observed when an extra thymidine nucleotide was incorporated in the complementary strand.

  DOI：

  10.3891/acta.chem.scand.51-0318
• 作为产物：
  描述：

  5'-O-tritylthymidine 在 吡啶 、 sodium tetrahydroborate 、 二异丁基氢化铝 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 生成 3'-Deoxy-3'-C-(acetoxymethyl)thymidine
  参考文献：
  名称：

  5'-膦酸酯连接的胸苷脱氧寡核苷酸的合成

  摘要：

  合成了5'-脱氧-5'-膦基胸苷，并与3'-脱氧-3'-羟基-甲基胸苷偶联，得到3'-CO-5P-5'连接的胸苷二核苷酸。该二聚体作为其3'-亚磷酰胺被用于合成脱氧寡核苷酸。

  DOI：

  10.1016/0040-4039(96)01437-2

文献信息

• Heteroatomic oligonucleoside linkages
  申请人：Isis Pharmaceuticals, Inc.

  公开号：US06087482A1

  公开（公告）日：2000-07-11

  Oligonucleotide-mimicking macromolecules that have improved nuclease resistance are provided. Replacement of the normal phosphorodiester inter-sugar linkages found in natural oligonucleotides with four atom linking groups provide unique compounds that are useful in regulating RNA expression and in therapeutics. Methods of synthesis and use also are disclosed.

  提供了具有改进核酸酶抗性的寡核苷酸模拟大分子。用四个原子连接基取代天然寡核苷酸中的正常磷酸二酯间糖连接，提供了独特的化合物，可用于调节RNA表达和治疗。还公开了合成和使用方法。
• An Extended Phosphate Linkage: Synthesis, Hybridization and Modeling Studies of Modified Oligonucleotides
  作者：Becky Haly、Laurent Bellon †、Venkatraman Mohan、Yogesh Sanghvi

  DOI：10.1080/07328319608002438

  日期：1996.7

  Novel stretched oligonucleotides (A-D) containing a 3'-alpha-C-methylene phosphodiester bridge (5-atoms long) have been synthesized on an automated synthesizer utilizing phosphoramidite chemistry. The key building-block 1-[3 ''-O-beta-cyanoethyldiisopropylaminophosphiryl-2,3 -dideoxy-5-O-dimethoxytriphenylmethyl-3-C-(hydroxymethyl)-beta-D-erythro-pentofuranosyl]thymine (21) was prepared in a stereoselective manner from thymidine. Hybridization studies indicated a drop (1.8-3.0 degrees C/mod.) in affinity for the complementary RNA and DNA targets. Molecular modeling results indicated that the 5-atom modified backbone had a different geometry around the phosphodiester linkage compared to the natural phosphodiester linkage. The stretched backbone may not be useful for antisense or tripler constructs, however it may find applications in biochemical/enzyme studies.
• US6087482A
  申请人：——

  公开号：US6087482A

  公开（公告）日：2000-07-11
• [EN] HETEROATOMIC OLIGONUCLEOSIDE LINKAGES<br/>[FR] LIAISONS PAR OLIGONUCLEOCIDES HETEROATOMIQUES
  申请人：——

  公开号：WO1994022886A1

  公开（公告）日：1994-10-13

  [EN] Oligonucleotide-mimicking macromolecules that have improved nuclease resistance are provided. Replacement of the normal phosphorodiester inter-sugar linkages found in natural oligonucleotides with four atom linking groups provide unique compounds that are useful in regulating RNA expression and in therapeutics. Methods of synthesis and use also are disclosed.
  [FR] L'invention se rapporte à des macromolécules imitant les oligonucléotides, qui sont pourvues d'une plus grande résistance aux nucléases. Le remplacement des liaisons inter-sucres de phosphorodiester normales se trouvant dans les oligonucléotides naturels par quatre groupes de liaison d'atomes permettent de former des composés uniques qui sont utiles dans la régulation de l'expression d'ARN et à des fins thérapeutiques. Des procédés de synthèse et d'utilisation sont également décrits.
• Synthesis of 5′-phosphonate linked thymidine deoxyoligonucleotides
  作者：Thomas Kofoed、Marvin H. Caruthers

  DOI：10.1016/0040-4039(96)01437-2

  日期：1996.9

  idine was synthesized and coupled with 3′-deoxy-3′-hydroxy-methylthymidine to yield a 3′-COP-5′ linked thymidine dinucleotide. This dimer as its 3′-phosphoramidite was used to synthesize deoxyoligonucleotides.

  合成了5'-脱氧-5'-膦基胸苷，并与3'-脱氧-3'-羟基-甲基胸苷偶联，得到3'-CO-5P-5'连接的胸苷二核苷酸。该二聚体作为其3'-亚磷酰胺被用于合成脱氧寡核苷酸。