(2S,3R,5R)-2-(羟基甲基)-5-(5-甲基-2,4-二氧代嘧啶-1-基)四氢呋喃-3-甲腈 | 116195-58-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 中文名称: (2S,3R,5R)-2-(羟基甲基)-5-(5-甲基-2,4-二氧代嘧啶-1-基)四氢呋喃-3-甲腈
• 英文名称: 3'-cyano-3'-deoxythymidine
• 英文别名: 3'-C-cyano-3'-deoxythymidine；Cyanothymidine；(2S,3R,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolane-3-carbonitrile
• CAS: 116195-58-5
• 化学式: C₁₁H₁₃N₃O₄
• 分子量: 251.242
• InChiKey: LFAIUPXHKWZRNL-IWSPIJDZSA-N

物化性质

• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3R,5R)-2-(羟基甲基)-5-(5-甲基-2,4-二氧代嘧啶-1-基)四氢呋喃-3-甲腈 在 dimethyl ammonium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 以74%的产率得到3'-deoxy-3'-(1H-tetrazol-5-yl)thymidine
  参考文献：
  名称：

  摘要：

  Thymidine dimers in which the natural phosphodiester linkage has been replaced by a 2,5-disubstituted tetrazole ring are synthesized and incorporated into oligodeoxynucleotides (ODNs). The synthesis is accomplished by two strategies based on an alkylation of 5'-O-trityl-on and 5'-O-trityl-off 3'-deoxy-3'-(1H-tetrazol-5-vl)thymidines with 5'-iodo-5'-deoxythymidine in the presence of Et3N. and the formation of only 2-substituted tetrazol-5-yl linkages is observed in 89 and 46% yields. respectively. The nucleoside dimer formed is reacted with 4,4'-dimethoxytrityl chloride (DMTCI), followed by treatment with 2-cyanoethyl tetraisopropyl-phosphordiamidite in the presence of NN-diisopropylammonium tetrazolide, to afford the 5'-O-DMT-protecteci dinucleoside phosphoramidite that is used for incorporation into ODNs on an automated DNA synthesizer. The modified ODNs with one and up to five tetrazole internucleosidic linkages are obtained in good yields. The thermal stability of DNA/DNA and DNA/RNA duplexes is studied by UV experiments and reported also.

  DOI：

  10.1002/1522-2675(200209)85:9<2847::aid-hlca2847>3.0.co;2-1
• 作为产物：
  描述：

  5-甲基尿甙 在 chromium(VI) oxide 、 盐酸 、 甲醇 、 sodium hydroxide 、 phenoxy-thiocarbonyl chloride 、 偶氮二异丁腈 、 四丁基氟化铵 、 三正丁基氢锡 、 乙酸酐 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 水 为溶剂， 生成 (2S,3R,5R)-2-(羟基甲基)-5-(5-甲基-2,4-二氧代嘧啶-1-基)四氢呋喃-3-甲腈
  参考文献：
  名称：

  3′--Cyano-3′-deoxythymidine

  摘要：

  DOI：

  10.1016/s0040-4039(00)82488-0

文献信息

• Methyl 5-0--butyldiphenylsilyl-2-deoxy-α β -d--pentofuranoside as a divergent intermediate for the synthesis of 3'-substituted-2',3'-dideoxynucleosides: synthesis of 3'-azido-3'-deoxythymidine, 3'-deoxy-3'-fluorothymidine and 3'-cyano-3'-deoxythymidine.
  作者：George W.J. Fleet、Jong Chan Son、Andrew E. Derome

  DOI：10.1016/s0040-4020(01)85850-6

  日期：1988.1

  The use of methyl 5-0--butyldiphenylsilyl-2-deoxy-α , β -D--pentofuranoside, prepared from D-xylose,as a divergent intermediate for the synthesis of 3'-substituted-2',3'-dideoxynucleosides is illustrated by its conversion into 3'-azido-3'-deoxythymidine, 3'-deoxy-3'-fluorothymidine and 3'-cyano-3'-deoxythymidine.

  由D-木糖制得的甲基5-0-丁基二苯基甲硅烷基-2-脱氧-α，β-D-五呋喃糖苷作为合成3'-取代的2'，3'-二脱氧核苷的发散中间体的用途通过将其转化为3'-叠氮基-3'-脱氧胸苷，3'-脱氧-3'-氟胸苷和3'-氰基-3'-脱氧胸苷来举例说明。
• Synthesis of chemically reactive analogues of AZT and their biological evaluation against HIV
  作者：Stuart L. Schreiber、Norihiro Ikemoto

  DOI：10.1016/0040-4039(88)85124-4

  日期：1988.1

  Several 3'-deoxythymidine analogues were prepared and tested against HIV. The choice of analogues was based on their possible covalent binding to the enzyme reverse transcriptase.

  制备了几种3'-脱氧胸苷类似物，并针对HIV进行了测试。类似物的选择基于它们与酶逆转录酶的可能共价结合。
• A short synthesis of 3'-cyano-3'-deoxythxmidine
  作者：K.E.B Parkes+、K Taylor

  DOI：10.1016/0040-4039(88)85069-x

  日期：1988.1

  A short synthesis of the nucleoside analogue 3'-cyano-3'-deoxy-thymidine, using free radical chemistry to introduce the nitrile function, is described.

  描述了使用自由基化学引入腈功能的核苷类似物3'-氰基-3'-脱氧胸苷的简短合成。
• 1-(3-Cyano-2,3-dideoxy-.beta.-D-erythro-pentofuranosyl)thymine (cyanothymidine): synthesis and antiviral evaluation against human immunodeficiency virus
  作者：Colin W. Greengrass、David W. T. Hoople、Stephen D. A. Street、Fiona Hamilton、Michael S. Marriott、Jon Bordner、Angus G. Dalgleish、Hiroaki Mitsuya、Samuel Broder

  DOI：10.1021/jm00123a019

  日期：1989.3

  1-(3-Cyano-2,3-dideoxy-beta-D-erythro-pentofuranosyl)thymine (cyanothymidine) (3a) has been prepared by an unambiguous route starting from D-xylose. The relative and absolute stereochemistry of 3a and its anomeric isomer 9 have been confirmed by NOE experiments and by X-ray diffraction analysis. In antiviral tests vs HIV 3a was shown to be inactive, a surprising result in view of a preliminary disclosure claiming potent anti-HIV activity. The activity previously assigned to 3a is believed to be due to contamination of that sample with the known antiviral nucleoside analogue 5b.
• Synthesis of 3'--cyano-3'-deoxy- pentofuranosylthymine nucleosides
  作者：Ana Calvo-Mateo、Maria-José Camarasa、Angel Díaz-Ortíz、Federico G. De las Heras、Antonio Alemany

  DOI：10.1016/s0040-4020(01)86194-9

  日期：1988.1