1-<2,3-dideoxy-3-(uracil-1-yl)-β-D-threo-pentofuranosyl>thymine | 204688-11-9

• 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-<2,3-dideoxy-3-(uracil-1-yl)-β-D-threo-pentofuranosyl>thymine
• 英文别名: 1-[2',3'-dideoxy-3'(uracyl-1-yl)-β-D-threo-pentofuranosyl]thymine；1-[(2R,4R,5S)-4-(2,4-dioxopyrimidin-1-yl)-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 204688-11-9
• 化学式: C₁₄H₁₆N₄O₆
• 分子量: 336.304
• InChiKey: UPXNIXLLISYETL-FXPVBKGRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  128
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-<2,3-dideoxy-3-(uracil-1-yl)-β-D-threo-pentofuranosyl>thymine 在 硫酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 64.0h， 生成 2,3-dideoxy-3-(uracil-1-yl)-β-D-threo-pentopyranose 、 2,3-dideoxy-3-(uracil-1-yl)-α-D-threo-pentopyranose 、 1-<2,3-dideoxy-3-(uracil-1-yl)-β-D-threo-pentopyranosyl>thymine
  参考文献：
  名称：

  Acyclic nucleoside analogues from thymine-substituted thymidines and related compounds

  摘要：

  Hydrolysis of 3'-deoxy-3'-(thymin-1-yl)thymidine, 3'-deoxy-3'-(uracil-1-yl)thymidine, and related furanoses with two nucleobases has been investigated. 3'-beta-Substituted analogues, but not the 3'-alpha-substituted ones, afford isomeric pyranose nucleosides as intermediates, which have been isolated (6c and 6d). Reduction of the hydrolysis products with sodium borohydride afford the corresponding acyclic compounds (2'-deoxy-D-ribitol or D-ribitol derivatives), which have been fully characterised as their peracetates. (C) 1999 Elsevier Science Ltd. AII rights reserved.

  DOI：

  10.1016/s0040-4020(99)00310-5
• 作为产物：
  描述：

  5'-O-tritylthymidine 在 四氢吡咯 、 4-二甲氨基吡啶 、 硫酸 、 叠氮磷酸二苯酯 、 苯硫酚 、 三乙胺 、 三苯基膦 、 tin(ll) chloride 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 、 苯 为溶剂， 反应 18.67h， 生成 1-<2,3-dideoxy-3-(uracil-1-yl)-β-D-threo-pentofuranosyl>thymine
  参考文献：
  名称：

  尿嘧啶和胸腺嘧啶取代的胸苷和尿苷衍生物

  摘要：

  3'-脱氧胸苷的四种可能的3'-尿嘧啶-1-基和3'-胸腺嘧啶-1-基衍生物以及2'-脱氧尿苷的四种类似衍生物已分别从胸苷和尿苷合成。公开了相对于H 2 / Pd，2-（甲氧基羰基）乙烯基防止H 2 / Pd形成脱水核苷的优点和SnCl 2 / PhSH / Et 3 N减少大多数叠氮基的优点。

  DOI：

  10.1016/s0040-4039(98)00100-2

文献信息

• Uracil- and thymine-substituted thymidine and uridine derivatives
  作者：Anna M. Costa、Montserrat Faja、Jaume Farràs、Jaume Vilarrasa

  DOI：10.1016/s0040-4039(98)00100-2

  日期：1998.3

  The four possible 3′-uracil-1-yl and 3′-thymin-1-yl derivatives of 3′-deoxythymidine and the four analogous derivatives of 2′-deoxyuridine have been synthesised from thymidine and uridine, respectively. Advantages of the 2-(methoxycarbonyl)vinyl group to prevent the formation of anhydronucleosides and of SnCl2/PhSH/Et3N in relation to H2/Pd for the reduction of most azido groups are disclosed.

  3'-脱氧胸苷的四种可能的3'-尿嘧啶-1-基和3'-胸腺嘧啶-1-基衍生物以及2'-脱氧尿苷的四种类似衍生物已分别从胸苷和尿苷合成。公开了相对于H 2 / Pd，2-（甲氧基羰基）乙烯基防止H 2 / Pd形成脱水核苷的优点和SnCl 2 / PhSH / Et 3 N减少大多数叠氮基的优点。
• Acyclic nucleoside analogues from thymine-substituted thymidines and related compounds
  作者：Anna M. Costa、Montserrat Faja、Jaume Vilarrasa

  DOI：10.1016/s0040-4020(99)00310-5

  日期：1999.5

  Hydrolysis of 3'-deoxy-3'-(thymin-1-yl)thymidine, 3'-deoxy-3'-(uracil-1-yl)thymidine, and related furanoses with two nucleobases has been investigated. 3'-beta-Substituted analogues, but not the 3'-alpha-substituted ones, afford isomeric pyranose nucleosides as intermediates, which have been isolated (6c and 6d). Reduction of the hydrolysis products with sodium borohydride afford the corresponding acyclic compounds (2'-deoxy-D-ribitol or D-ribitol derivatives), which have been fully characterised as their peracetates. (C) 1999 Elsevier Science Ltd. AII rights reserved.