(3R,4S,5S)-4-(azidomethyl)-5-(hydroxymethyl)oxolane-2,3-diol | 1025898-09-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: (3R,4S,5S)-4-(azidomethyl)-5-(hydroxymethyl)oxolane-2,3-diol
• CAS: 1025898-09-2
• 化学式: C₆H₁₁N₃O₄
• 分子量: 189.171
• InChiKey: JTDWBRISEWYXAL-JDJSBBGDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  84.3
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3R,4S,5S)-4-(azidomethyl)-5-(hydroxymethyl)oxolane-2,3-diol 在 吡啶 、 C₄F₉SO₃K 、 氨 、 silver nitrate 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 反应 75.0h， 生成 1-<3-C-(azidomethyl)-5-O-(tert-butyldimethylsilyl)-3-deoxy-2-O-(methylsulfonyl)-β-D-erythro-pentofuranosyl>thymine
  参考文献：
  名称：

  Syntheses and biological evaluations of 3'-deoxy-3'-C-branched-chain-substituted nucleosides

  摘要：

  Various 3'-deoxy-3'-C-(hydroxymethyl)-, 3'-deoxy-3'-C-(fluoromethyl)-, 3'-deoxy-3'-C-(azidomethyl)-, and 3'-deoxy-3'-C-(aminomethyl)-substituted nucleosides (total 12 compounds) have been synthesized and evaluated against L1210, P388, S-180, and CCRF-CEM cells and HSV-1, HSV-2, and HIV-1 in culture. Only 3'-deoxy-3'-C-(hydroxymethyl)thymidine (36) was found to show significant anticancer activity against L1210, P388, S-180, and CCRF-CEM cells with ED50 values of 50, 5, 10, and 1 muM, respectively. None of these compounds demonstrated significant antiviral activity against HSV-1, HSV-2, or HIV-1. These compounds were also evaluated against thymidine kinases derived from HSV-1 (strain KOS), HSV-2 (strain 333), and mammalian (K562) cells. The thymidine kinase (HSV-1 strain KOS) was inhibited significantly by both 3'-deoxy-3'-C-(hydroxymethyl)- and 3'-deoxy-3'-C-(fluoromethyl)thymidine.

  DOI：

  10.1021/jm00055a006
• 作为产物：
  描述：

  1,2-O-isopropylidene-5-O-(tert-butyl)dimethylsilyl-α-D-xylofuranoside 在 四氢呋喃 、 吡啶 、 chromium(VI) oxide 、 sodium hydroxide 、 叠氮化锂 、 硼烷 、 双氧水 、 乙酸酐 、 sodium hydride 、 溶剂黄146 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 35.5h， 生成 (3R,4S,5S)-4-(azidomethyl)-5-(hydroxymethyl)oxolane-2,3-diol
  参考文献：
  名称：

  Syntheses and biological evaluations of 3'-deoxy-3'-C-branched-chain-substituted nucleosides

  摘要：

  Various 3'-deoxy-3'-C-(hydroxymethyl)-, 3'-deoxy-3'-C-(fluoromethyl)-, 3'-deoxy-3'-C-(azidomethyl)-, and 3'-deoxy-3'-C-(aminomethyl)-substituted nucleosides (total 12 compounds) have been synthesized and evaluated against L1210, P388, S-180, and CCRF-CEM cells and HSV-1, HSV-2, and HIV-1 in culture. Only 3'-deoxy-3'-C-(hydroxymethyl)thymidine (36) was found to show significant anticancer activity against L1210, P388, S-180, and CCRF-CEM cells with ED50 values of 50, 5, 10, and 1 muM, respectively. None of these compounds demonstrated significant antiviral activity against HSV-1, HSV-2, or HIV-1. These compounds were also evaluated against thymidine kinases derived from HSV-1 (strain KOS), HSV-2 (strain 333), and mammalian (K562) cells. The thymidine kinase (HSV-1 strain KOS) was inhibited significantly by both 3'-deoxy-3'-C-(hydroxymethyl)- and 3'-deoxy-3'-C-(fluoromethyl)thymidine.

  DOI：

  10.1021/jm00055a006

文献信息

• Synthesis of an aza analogue of 2-deoxy-d-ribofuranose and its homologues
  作者：Vyacheslav V Filichev、Malene Brandt、Erik B Pedersen

  DOI：10.1016/s0008-6215(01)00132-x

  日期：2001.7

  Azasugars were obtained in one-pot reactions by catalytic reduction reactions of amino group precursors in aldosugars followed by intramolecular reductive amino alkylation reactions. (3R,4S)-4-[(1S)-1,2-Dihydroxyethyl]pyrrolidin-3-ol was obtained from D-xylose by two different strategies through 3-C-cyano-3-deoxy-D-ribo-pentofuranose or 3-C-azidomethyl-3-deoxy-D-ribo-pentofuranose in 6 and 16% overall

  一锅反应中的氮杂糖是通过醛糖中氨基前体的催化还原反应，然后进行分子内还原性氨基烷基化反应而获得的。（3R，4S）-4-[（1S）-1,2-二羟乙基]吡咯烷-3-醇是通过两种不同的策略通过3-C-氰基-3-脱氧-D-核糖-戊呋喃糖从D-木糖获得的或3-C-叠氮基甲基3-脱氧-D-核糖-戊呋喃糖，总收率分别为6％和16％。在相应的Fmoc-氮杂糖中二醇基团的氧化裂解，然后脱保护，得到（3R，4R）-4-（羟甲基）吡咯烷丁-3-醇。（3R，4S）-4-[（1S，2R）-1,2,3-三羟丙基]吡咯烷-3-醇是由双丙酮-D-葡萄糖通过3-脱氧-3-C-硝基甲基-D-阿洛糖合成的总产率为7％。
• Syntheses and biological evaluations of 3'-deoxy-3'-C-branched-chain-substituted nucleosides
  作者：Tai Shun Lin、Ju Liang Zhu、Ginger E. Dutschman、Yung Chi Cheng、William H. Prusoff

  DOI：10.1021/jm00055a006

  日期：1993.2

  Various 3'-deoxy-3'-C-(hydroxymethyl)-, 3'-deoxy-3'-C-(fluoromethyl)-, 3'-deoxy-3'-C-(azidomethyl)-, and 3'-deoxy-3'-C-(aminomethyl)-substituted nucleosides (total 12 compounds) have been synthesized and evaluated against L1210, P388, S-180, and CCRF-CEM cells and HSV-1, HSV-2, and HIV-1 in culture. Only 3'-deoxy-3'-C-(hydroxymethyl)thymidine (36) was found to show significant anticancer activity against L1210, P388, S-180, and CCRF-CEM cells with ED50 values of 50, 5, 10, and 1 muM, respectively. None of these compounds demonstrated significant antiviral activity against HSV-1, HSV-2, or HIV-1. These compounds were also evaluated against thymidine kinases derived from HSV-1 (strain KOS), HSV-2 (strain 333), and mammalian (K562) cells. The thymidine kinase (HSV-1 strain KOS) was inhibited significantly by both 3'-deoxy-3'-C-(hydroxymethyl)- and 3'-deoxy-3'-C-(fluoromethyl)thymidine.