3'-deoxy-3'-{{6-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-1-thiohexyl}amino}thymidine | 289706-31-6

• 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'-{{6-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-1-thiohexyl}amino}thymidine
• CAS: 289706-31-6
• 化学式: C₃₁H₃₆N₄O₆S
• 分子量: 592.716
• InChiKey: KKXXKJQKYAUKGZ-ZRRKCSAHSA-N

物化性质

• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.51
• 重原子数：
  42.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  134.68
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3'-deoxy-3'-{{6-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-1-thiohexyl}amino}thymidine 在 哌啶 、 吡啶 、 三正丁胺 、 (Bu₃NH)2P₂O₇ 、 水 、 碘 、 碳酸氢钠 作用下， 以 1,4-二氧六环 、 吡啶 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 3'-{{6-{{{[3-carboxy-4-(6-hydroxy-3-oxo-3H-xanthen-9-yl)phenyl]amino}thiomethyl}amino}-1-thioxohexyl}amino}-3'-deoxythymidine 5'-triphosphate
  参考文献：
  名称：

  摘要：

  The thioamide derivatives 3'-deoxy-5'- O-(4,4'-dimethoxytrityl)-3'-[ (2-methyl-1-thioxopropyl)amino] thymidine (4a) and 3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-3'-{{6-{[9H-(fluoren-9-ylmethoxy)carbonyl]amino}-1-thioxohexyl}amino}thymidine (4b) were synthesized by regioselective thionation of the corresponding amides 3a and 3b with 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide (Lawesson's reagent). The addition of exact amounts of pyridine to the reaction mixture proved to be essential for an efficient transformation. The thioamides were converted into the corresponding 5'-triphosphates 6a and 6b. Compound 6a was chosen for DNA sequencing experiments, and 6b was further labelled with fluorescein (-->8).

  DOI：

  10.1002/1522-2675(20000607)83:6<1268::aid-hlca1268>3.0.co;2-s
• 作为产物：
  描述：

  3'-azido-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)thymidine 在 platinum(IV) oxide 劳森试剂 、 吡啶 、 水 、 氢气 、 O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 3'-deoxy-3'-{{6-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-1-thiohexyl}amino}thymidine
  参考文献：
  名称：

  摘要：

  The thioamide derivatives 3'-deoxy-5'- O-(4,4'-dimethoxytrityl)-3'-[ (2-methyl-1-thioxopropyl)amino] thymidine (4a) and 3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-3'-{{6-{[9H-(fluoren-9-ylmethoxy)carbonyl]amino}-1-thioxohexyl}amino}thymidine (4b) were synthesized by regioselective thionation of the corresponding amides 3a and 3b with 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide (Lawesson's reagent). The addition of exact amounts of pyridine to the reaction mixture proved to be essential for an efficient transformation. The thioamides were converted into the corresponding 5'-triphosphates 6a and 6b. Compound 6a was chosen for DNA sequencing experiments, and 6b was further labelled with fluorescein (-->8).

  DOI：

  10.1002/1522-2675(20000607)83:6<1268::aid-hlca1268>3.0.co;2-s

文献信息

• SYNTHESIS OF 3′-THIOAMIDO-MODIFIED 3′-DEOXYTHYMIDINE-5′-TRIPHOSPHATES AND THEIR USE AS CHAIN TERMINATORS IN SANGER-DNA SEQUENCING
  作者：K. Schwarzer、C. Wojczewski、J. W. Engels

  DOI：10.1081/ncn-100002450

  日期：2001.3.31

  The thioamide derivatives 3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-3'-[(2-methyl-1-thioxo-propyl)amino]thymidine 1 and 3'-deoxy-5'-O-(4,4'-dimethoxytrityl) -3'- 6-[(9H-(fluo-ren-9-ylmethoxy)carbonyl] -amino}-1-thioxohexyl}amino} thymidine 2 were synthesized by regioselective thionation of their corresponding amides 7 and 8 with 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane- 2,4-disulfide (Lawesson's reagent). The thioamides were converted into the corresponding 5'-triphosphates 3 and 4. Compound 3 was chosen for DNA sequencing experiments and 4 was further labelled with fluorescein.