1-(2,3-anhydro-β-D-lyxofuranosyl)thymine | 14486-22-7

• 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-(2,3-anhydro-β-D-lyxofuranosyl)thymine
• 英文别名: 1-[(1S,2R,4R,5S)-4-(hydroxymethyl)-3,6-dioxabicyclo[3.1.0]hexan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 14486-22-7
• 化学式: C₁₀H₁₂N₂O₅
• 分子量: 240.216
• InChiKey: AXBTVCCVDAUCIY-UTSKPXGSSA-N

物化性质

• 熔点：
  143.5-144.5 °C
• 密度：
  1.505±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  91.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  二乙基氰化铝 、 1-(2,3-anhydro-β-D-lyxofuranosyl)thymine 以 四氢呋喃 、 甲苯 为溶剂， 反应 0.33h， 以32%的产率得到3'-cyano-3'-deoxy-β-D-arabinofuranosylthymine
  参考文献：
  名称：

  Synthesis of 3′-Cyano-3′-deoxy-β-D-arabino-nucleosides

  摘要：

  报道了通过氰基二乙基铝与木酮型环氧的区域选择性环裂解合成3′-氰基-3′-脱氧-β-D-阿拉伯糖核苷的方法。

  DOI：

  10.1055/s-1988-27760
• 作为产物：
  描述：

  O,O-二(三甲基甲硅烷基)胸苷 在 N-碘代丁二酰亚胺 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 26.0h， 生成 1-(2,3-anhydro-β-D-lyxofuranosyl)thymine
  参考文献：
  名称：

  An efficient and highly stereoselective synthesis of nucleoside derivatives from furanoid 1,2-diols

  摘要：

  Reaction between suitably protected furanoid glycals 1b-4b, readily obtained from furanoid 1,2-diols (1a-4a), and different silylated pyrimidine bases, gave the corresponding 3',5'- and 3',5',6'-O-protected 2'-deoxy-2'-iodo-beta-D-xylo-pentofuranosyl 5-10 and beta-D-gluco-hexofuranosyl 11 nucleosides, respectively. Compound 5 has been transformed into its 2'-deoxy 12 and 2',3'-anhydro 14 derivatives. The high stereoselectivity of the reaction is discussed. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00332-7

文献信息

• 1-(2,3-Anhydro-.beta.-D-lyxofuranosyl)cytosine derivatives as potential inhibitors of the human immunodeficiency virus
  作者：Thomas R. Webb、Hiroaki Mitsuya、Samuel Broder

  DOI：10.1021/jm00402a038

  日期：1988.7

  We report here that 1-(2,3-anhydro-beta-D-lyxofuranosyl)cytosine has activity against the human immunodeficiency virus in vitro. A number of 2',3'-anhydro-beta-D-lyxofuranosyl nucleoside derivatives were prepared, but none had the activity of the title compound. New efficient procedures were developed for the synthesis of 3'-deoxy-3'-alkyl- and 3'-deoxy-beta-D-arabinosylpyrimidine derivatives.

  我们在这里报告1-（2,3-脱水-β-D-呋喃糖基）胞嘧啶在体外对人免疫缺陷病毒具有活性。制备了许多2'，3'-脱水-β-D-呋喃呋喃糖基核苷衍生物，但没有一个具有标题化合物的活性。开发了用于合成3'-脱氧-3'-烷基-和3'-脱氧-β-D-阿拉伯糖基嘧啶衍生物的新的有效程序。
• Reactivity of 2',3'-Anhydro Pyrimidine Nucleosides toward Trimethylaluminum
  作者：Kosaku Hirota、Hideki Takasu、Hironao Sajiki

  DOI：10.3987/com-99-s144

  日期：——

  Treatment of 2',3'-anhydro pyrimidine nucleoside derivatives (1) with trimethylaluminum afforded 1-(3-deoxy-3-methyl-beta-D-arabinofuranosyl)pyrimidine derivatives (2) and 1-(2-deoxy-2-methyl-beta-D-xylofuranosyl)pyrimidine derivatives (3) as a mixture in approximately 2 : 1 - 3 : 1 ratio via ring-opening of the epoxide involving the nucleophilic attack of trimethylaluminum at the 3' or 2'-position of 1.
• Synthesis of 3′-Cyano-3′-deoxy-β-D-<i>arabino</i>-nucleosides
  作者：Dieter Häbich、Wolfgang Barth

  DOI：10.1055/s-1988-27760

  日期：——

  The synthesis of 3′-cyano-3′-deoxy-β-D-arabino-nucleosides by regioselective ring cleavage of lyxo-epoxides with cyanodiethylalane is described.

  报道了通过氰基二乙基铝与木酮型环氧的区域选择性环裂解合成3′-氰基-3′-脱氧-β-D-阿拉伯糖核苷的方法。
• An efficient and highly stereoselective synthesis of nucleoside derivatives from furanoid 1,2-diols
  作者：Rafael Robles、concepción Rodríguez、Isidoro Izquierdo、María T. Plaza、Antonio Mota

  DOI：10.1016/s0957-4166(97)00332-7

  日期：1997.9

  Reaction between suitably protected furanoid glycals 1b-4b, readily obtained from furanoid 1,2-diols (1a-4a), and different silylated pyrimidine bases, gave the corresponding 3',5'- and 3',5',6'-O-protected 2'-deoxy-2'-iodo-beta-D-xylo-pentofuranosyl 5-10 and beta-D-gluco-hexofuranosyl 11 nucleosides, respectively. Compound 5 has been transformed into its 2'-deoxy 12 and 2',3'-anhydro 14 derivatives. The high stereoselectivity of the reaction is discussed. (C) 1997 Elsevier Science Ltd.