3'-C-amino-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-3-N,5'(R)-C-ethylenethymidine | 246538-23-8

• 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'-C-amino-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-3-N,5'(R)-C-ethylenethymidine
• 英文别名: 1-[(2R,3aS,7R,7aS)-7-[bis(4-methoxyphenyl)-phenylmethoxy]-2,3,3a,4,5,6,7,7a-octahydrofuro[3,2-b]pyridin-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 246538-23-8
• 化学式: C₃₃H₃₅N₃O₆
• 分子量: 569.657
• InChiKey: YXVUETWCRBRDCM-KJHMZRPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  42
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  98.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3'-C-amino-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-3-N,5'(R)-C-ethylenethymidine 在 4-二甲氨基吡啶 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 21.5h， 生成 [(2R,3S,5R)-3-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl (2R,3aS,7R,7aS)-7-[bis(4-methoxyphenyl)-phenylmethoxy]-2-(5-methyl-2,4-dioxopyrimidin-1-yl)-3,3a,5,6,7,7a-hexahydro-2H-furo[3,2-b]pyridine-4-carboxylate
  参考文献：
  名称：

  Conformationally Locked Nucleosides. Synthesis of Oligodeoxynucleotides Containing 3′-Amino-3′-deoxy-3′-N,5′(R)-C-ethylenethymidine

  摘要：

  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.

  DOI：

  10.1080/15257770008033851
• 作为产物：
  描述：

  齐多夫定 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 氢气 、 sodium carbonate 、 silver nitrate 、 二甲基亚砜 、 三乙胺 、 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 74.5h， 生成 3'-C-amino-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-3-N,5'(R)-C-ethylenethymidine
  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 and stereochemical assignments of 3′-N,5′-C-bridged 3′-amino-3′-deoxythymidines
  作者：Guangyi Wang

  DOI：10.1016/s0040-4039(99)01205-8

  日期：1999.8

  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.
• 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.