1-(3-azido-2,3-dideoxy-β-D-arabino-hexofuranosyl)thymine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-(3-azido-2,3-dideoxy-β-D-arabino-hexofuranosyl)thymine
• 英文别名: 1-(3-azido-2,3-dideoxy-beta-D-ribo-hexofuranosyl)thymine；1-[(2R,4R,5S)-4-azido-5-[(1R)-1,2-dihydroxyethyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• 化学式: C₁₁H₁₅N₅O₅
• 分子量: 297.271
• InChiKey: JXDNQHJWBNFXQG-BGZDPUMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  O,O-二(三甲基甲硅烷基)胸苷 在 三氟甲磺酸三甲基硅酯 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 25.5h， 生成 1-(3-azido-2,3-dideoxy-β-D-arabino-hexofuranosyl)thymine
  参考文献：
  名称：

  Synthesis of 2′,3′-Dideoxy-D-erythro-hexofuranosyl Nucleosides and 3′-Azido-2′, 3′-dideoxy-D-arabino-hexofuranosyl Nucleosides From Tri-O-acetyl-D-glucal via an α,β-Unsaturated Hexose Aldehyde

  摘要：

  由三-O-乙酰基-D-葡萄糖制备的α,β-不饱和醛2经缩醛化和苯甲酰化得到α,β-不饱和缩醛6。双键氢化，随后甲醇解产生甲基2,3-二脱氧呋喃糖基糖苷8，其用于与甲硅烷基化的N 6-异丁酰胞嘧啶和甲硅烷基化的胸腺嘧啶进行核苷偶联。 受保护的3-叠氮基-2,3-二脱氧-阿拉伯-呋喃糖26 是通过将叠氮酸1,4-加成到二甲硅烷基化的α,β-不饱和醛24 上然后乙酰化来制备的。化合物26用于制备3'-叠氮基-2',3'-二脱氧-D-阿拉伯-呋喃己糖核苷28和29。

  DOI：

  10.1055/s-1991-28417

文献信息

• Synthesis of 2′,3′-Dideoxy-D-<i>erythro</i>-hexofuranosyl Nucleosides and 3′-Azido-2′, 3′-dideoxy-D-<i>arabino</i>-hexofuranosyl Nucleosides From Tri-<i>O</i>-acetyl-D-glucal via an α,β-Unsaturated Hexose Aldehyde
  作者：Jesper Lau、Jesper Wengel、Erik B. Pedersen、Bent Faber Vestergaard

  DOI：10.1055/s-1991-28417

  日期：——

  α,β-Unsaturated aldehyde 2 prepared from tri-O-acetyl-D-glucal was acetalated and benzoylated to give α,β-unsaturated acetal 6. Hydrogenation of the double bond followed by methanolysis resulted in methyl 2,3-dideoxyfuranosyl glycoside 8 which was used for nucleoside coupling with silylated N 6-isobutyrylcytosine and silylated thymine. Protected 3-azido-2,3-dideoxy-arabino-furanose 26 was prepared by 1,4-addition of hydrazoic acid to disilylated α,β-unsaturated aldehyde 24 followed by acetylation. Compound 26 was used for the preparation of 3′-azido-2′,3′-dideoxy-D-arabino-hexofuranosyl nucleosides 28 and 29.

  由三-O-乙酰基-D-葡萄糖制备的α,β-不饱和醛2经缩醛化和苯甲酰化得到α,β-不饱和缩醛6。双键氢化，随后甲醇解产生甲基2,3-二脱氧呋喃糖基糖苷8，其用于与甲硅烷基化的N 6-异丁酰胞嘧啶和甲硅烷基化的胸腺嘧啶进行核苷偶联。 受保护的3-叠氮基-2,3-二脱氧-阿拉伯-呋喃糖26 是通过将叠氮酸1,4-加成到二甲硅烷基化的α,β-不饱和醛24 上然后乙酰化来制备的。化合物26用于制备3'-叠氮基-2',3'-二脱氧-D-阿拉伯-呋喃己糖核苷28和29。
• Synthesis of 1-(3-Azido-2,3-Dideoxy-Beta-D-Ribo-Hexofuranosyl)Thymine
  作者：Merrick R. Almond、Gregory T. Lowen、Gary E. Martin、Janet L. Rideout

  DOI：10.1080/07328319308018561

  日期：1993.11

  The nucleoside derivative 1-(3-azido-2,3-dideoxy-beta-D-ribo-hexofuranosyl)thymine has been synthesized from 3-O-benzyl-1,2-O-isopropylidene-alpha-D-glucofuranose-5,6-carbonate in an overall yield of 16%. The key step in the synthesis involves the selective deacetylation of a nucleoside derivative having a cyclic carbonate moiety.