3-[(2S,3S,5R)-3-Benzyloxycarbonylamino-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-3-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-propionic acid ethyl ester | 246538-35-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 3-[(2S,3S,5R)-3-Benzyloxycarbonylamino-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-3-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-propionic acid ethyl ester
• CAS: 246538-35-2
• 化学式: C₄₃H₄₅N₃O₁₀
• 分子量: 763.844
• InChiKey: AAOZVPCYUIAPAI-XUGGJDEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.78
• 重原子数：
  56.0
• 可旋转键数：
  15.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  156.41
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  3-[(2S,3S,5R)-3-Benzyloxycarbonylamino-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-3-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-propionic acid ethyl ester 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 四丁基氟化铵 、 氢气 、 silver trifluoromethanesulfonate 、 4-甲基苯磺酸吡啶 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 82.5h， 生成
  参考文献：
  名称：

  Conformationally locked nucleosides. Synthesis and stereochemical assignments of 3′-N,5′-C-bridged 3′-amino-3′-deoxythymidines

  摘要：

  3'-Amino-3'-deoxythymidine was converted, in multi-steps, to its 5'-O-(4,4'-dimethoxytrityl)-5'-C-tosyl-oxyethyl-3'-N-carbobenzoxy derivative 7 and 5'-C-mesyloxyethyl-3'-N-(9-fluorenyl)methoxycarbonyl derivatives 6 and 11. Subsequent hydrogenolysis or treatment with DMAP afforded 3'-N,5'-C-bridged bicyclic thymidines. Stereochemical assignments were accomplished with the help of NOE. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01205-8
• 作为产物：
  描述：

  齐多夫定 在 palladium on activated charcoal 吡啶 、 氢气 、 sodium carbonate 、 silver nitrate 、 二甲基亚砜 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 、 锌 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 55.0h， 生成 3-[(2S,3S,5R)-3-Benzyloxycarbonylamino-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-3-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-propionic acid ethyl ester
  参考文献：
  名称：

  Conformationally locked nucleosides. Synthesis and stereochemical assignments of 3′-N,5′-C-bridged 3′-amino-3′-deoxythymidines

  摘要：

  3'-Amino-3'-deoxythymidine was converted, in multi-steps, to its 5'-O-(4,4'-dimethoxytrityl)-5'-C-tosyl-oxyethyl-3'-N-carbobenzoxy derivative 7 and 5'-C-mesyloxyethyl-3'-N-(9-fluorenyl)methoxycarbonyl derivatives 6 and 11. Subsequent hydrogenolysis or treatment with DMAP afforded 3'-N,5'-C-bridged bicyclic thymidines. Stereochemical assignments were accomplished with the help of NOE. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01205-8

文献信息

• Conformationally Locked Nucleosides. Synthesis of Oligodeoxynucleotides Containing 3′-Amino-3′-deoxy-3′-N,5′(R)-C-ethylenethymidine
  作者：Guangyi Wang、Vesna Stoisavljevic

  DOI：10.1080/15257770008033851

  日期：2000.9

  3'-Amino-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-3'-N,5(R)-C-ethylenethymidine (6)was synthesized starting from 3'-azido-3'-deoxythymidine. Condensation of 6 with 5'-O-(H-phosphonyl)thymidine and 5'-O-(p-nitrophenoxycarbonyl)thymidine derivatives gave dinucleotide and dinucleoside derivatives, respectively, which were incorporated into oligodeoxynucleotides (ODNs). Tm data of the modified ODNs are also presented.