1-(3-cyano-2,3-dideoxy-α-D-erythro-pentofuranosyl)-thymine | 116195-59-6

• 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: 1-(3-cyano-2,3-dideoxy-α-D-erythro-pentofuranosyl)-thymine
• 英文别名: Thymidine, 3'-cyano-3'-deoxy-；(2S,3R,5S)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolane-3-carbonitrile
• CAS: 116195-59-6
• 化学式: C₁₁H₁₃N₃O₄
• 分子量: 251.242
• InChiKey: LFAIUPXHKWZRNL-HLTSFMKQSA-N

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

• 作为产物：
  描述：

  2-deoxy-1-O-methyl-5-O-(4-methylbenzoyl)-3-O-<(trifluoromethyl)sulfonyl>-D-threo-pentofuranoside 在 三氟甲磺酸三甲基硅酯 、 potassium carbonate 、 牛血清白蛋白 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 6.75h， 生成 1-(3-cyano-2,3-dideoxy-α-D-erythro-pentofuranosyl)-thymine
  参考文献：
  名称：

  1-(3-Cyano-2,3-dideoxy-.beta.-D-erythro-pentofuranosyl)thymine (cyanothymidine): synthesis and antiviral evaluation against human immunodeficiency virus

  摘要：

  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.

  DOI：

  10.1021/jm00123a019

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 the dideoxynucleosides "ddC" and "CNT" from glutamic acid, ribonolactone, and pyrimidine bases
  作者：Masami Okabe、Ruen Chu Sun、Steve Y. K. Tam、Louis J. Todaro、David L. Coffen

  DOI：10.1021/jo00255a021

  日期：1988.9
• OKABE, MASAMI;SUN, RUEN-CHU;TAM, STEVE Y. K.;TODARO-LOUIS, J.;COFFEN, DAV+, J. ORG. CHEM., 53,(1988) N 20, C. 4780-4786
  作者：OKABE, MASAMI、SUN, RUEN-CHU、TAM, STEVE Y. K.、TODARO-LOUIS, J.、COFFEN, DAV+

  DOI：——

  日期：——