9-(3,5-di-O-mesyl-2,3,5-trideoxy-β-D-threo-pentofuranosyl)thymidine | 140175-72-0

• 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: 9-(3,5-di-O-mesyl-2,3,5-trideoxy-β-D-threo-pentofuranosyl)thymidine
• 英文别名: 1-(2-deoxy-3,5-di-O-mesyl-β-D-threo-pentofuranosyl)thymine；[(2R,3R,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-3-methylsulfonyloxyoxolan-2-yl]methyl methanesulfonate
• CAS: 140175-72-0
• 化学式: C₁₂H₁₈N₂O₉S₂
• 分子量: 398.415
• InChiKey: JPBRYDQRCOMYRY-OPRDCNLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.55
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  150.83
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  9-(3,5-di-O-mesyl-2,3,5-trideoxy-β-D-threo-pentofuranosyl)thymidine 在 叠氮化锂 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以73%的产率得到3',5'-diazido-2',3',5'-trideoxythymidine
  参考文献：
  名称：

  带正电的脱氧核胍 (DNG) 的固相合成束缚 Hoechst 33258 类似物：通过同时小槽结合的三链和双链稳定

  摘要：

  脱氧核胍 (DNG) 是一种 DNA 类似物，其中带正电荷的胍取代了磷酸二酯键，通过不同长度与 Hoechst 33258 荧光团相连。在固相上以 3' --> 5' 方向合成了五聚体胸苷 DNG，允许使用 PyBOP/HOBt 化学在 5'-末端逐步掺入直链氨基酸接头和双苯并咪唑 (Hoechst 33258) 配体. (DNA)(2).DNG-H 三链体和 DNA.DNG-H 双链体的稳定性由 DNG 和 DNG-Hoechst 33258 (DNG-H) 偶联物​​与 30 聚体双链 (ds) DNA、d(CGCCGCGCGCGCGAAAAACCCGGCGCGCGC) 形成)/d(GCGGCGCGCGCGCTTTTTGGGCCGCGCGCG) 和单链 (ss) DNA，5'-CGCCGCGCGCGCGAAAAACCCGGCGCGCGC-3'，分别通过热熔解和荧光发射实验进行了评估。在

  DOI：

  10.1021/ja031557s
• 作为产物：
  描述：

  甲基磺酰氯 、 threothymidine 在 吡啶 作用下， 以96%的产率得到9-(3,5-di-O-mesyl-2,3,5-trideoxy-β-D-threo-pentofuranosyl)thymidine
  参考文献：
  名称：

  带正电的脱氧核胍 (DNG) 的固相合成束缚 Hoechst 33258 类似物：通过同时小槽结合的三链和双链稳定

  摘要：

  脱氧核胍 (DNG) 是一种 DNA 类似物，其中带正电荷的胍取代了磷酸二酯键，通过不同长度与 Hoechst 33258 荧光团相连。在固相上以 3' --> 5' 方向合成了五聚体胸苷 DNG，允许使用 PyBOP/HOBt 化学在 5'-末端逐步掺入直链氨基酸接头和双苯并咪唑 (Hoechst 33258) 配体. (DNA)(2).DNG-H 三链体和 DNA.DNG-H 双链体的稳定性由 DNG 和 DNG-Hoechst 33258 (DNG-H) 偶联物​​与 30 聚体双链 (ds) DNA、d(CGCCGCGCGCGCGAAAAACCCGGCGCGCGC) 形成)/d(GCGGCGCGCGCGCTTTTTGGGCCGCGCGCG) 和单链 (ss) DNA，5'-CGCCGCGCGCGCGAAAAACCCGGCGCGCGC-3'，分别通过热熔解和荧光发射实验进行了评估。在

  DOI：

  10.1021/ja031557s

文献信息

• Solid-Phase synthesis of positively charged deoxynucleic guanidine (DNG) oligonucleotide mixed sequences
  作者：Putta Mallikarjuna Reddy、Thomas C. Bruice

  DOI：10.1016/s0960-894x(03)00119-7

  日期：2003.4

  Positively charged DNG oligonucleotide mixed sequences containing A/T bases were prepared by solid-phase synthesis. Synthesis proceeds in 3'-->5' direction and involves coupling of 3'-Fmoc protected thiourea in the presence of HgCl2/TEA with the corresponding 5'-amine of the growing oligo chain. DNG binding characteristics with complementary DNA and with itself have been evaluated. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Nucleoside sultones: synthons for the preparation of novel nucleotide analogs. 1. Synthesis and ring-opening reactions
  作者：Peter A. Crooks、Robert C. Reynolds、Joseph A. Maddry、Anita Rathore、M. Shamim Akhtar、John A. Montgomery、John A. Secrist

  DOI：10.1021/jo00036a014

  日期：1992.5

  Treatment of either the 5'-O-tosyl or the 5'-O-mesyl derivative of 3'-O-mesylthymidine with lithium acetylide-ethylenediamine complex in DMSO affords the intramolecular 6,3-ester of 1,2,5,6-tetradeoxy-l-(3,4-dihydro-5-methyl-2, 4-dioxo-1(2H)-pyrimidinyl)-beta-D-erythro-hexofuranuronosulfonic acid (2). Similarly, the 5'-O-tosyl or 5'-O-mesyl derivative of 1-(2-deoxy-3-O-mesyl-beta-D-threo-pentofuranosyl)thymine affords the intramolecular 6,3-ester of 1,2,5,6-tetradeoxy-1-(3,4-dihydro-5-methyl-2,4-dioxo-1(2H)-pyrimidinyl)-beta-D-threo-hexofuranurononsulfonic acid (5). Sultone 5 reacts with a variety of nucleophiles to afford good yields of the corresponding 3'-substituted sulfonate salts (6, 7, 9, and 10) and, in some cases, the unsaturated nucleoside 8. Sultone 2 was generally much less susceptible to ring opening by nucleophiles. However, in the presence of base, nucleophilic substitution with azide ion did proceed via the intermediate anhydronucleoside, 11, to afford 6. Reaction of 2 with EtOH-NaOH afforded a 1:1 mixture of the epimeric 3'-hydroxy compounds 9 and 12. The above sulfonate salts represent interesting new isosteres of nucleoside 5'-O-phosphates.