5-O-Benzoyl-2,3-dideoxy-2-fluoro-1-O-methyl-β-D-threo-pentofuranose | 136228-16-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-O-Benzoyl-2,3-dideoxy-2-fluoro-1-O-methyl-β-D-threo-pentofuranose
• 英文别名: methyl 5-O-benzoyl-2,3-dideoxy-2-fluoro-β-D-threo-pentafuranoside；1-0-methyl-5-0-benzoyl-2,3-dideoxy-2-fluoro-β-D-arabinofuranose；[(2S,4S,5R)-4-fluoro-5-methoxyoxolan-2-yl]methyl benzoate
• CAS: 136228-16-5
• 化学式: C₁₃H₁₅FO₄
• 分子量: 254.258
• InChiKey: SUKSJRDXIFYAOS-GMXVVIOVSA-N

物化性质

• 沸点：
  338.5±42.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-O-Benzoyl-2,3-dideoxy-2-fluoro-1-O-methyl-β-D-threo-pentofuranose 在 氢溴酸 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 5-O-benzoyl-2,3-dideoxy-2-fluoro-α-D-arabinofuranosyl bromide
  参考文献：
  名称：

  2'-氟-2'，3'-双脱氧阿拉伯呋喃糖基嘧啶的化学性质和抗HIV特性。

  摘要：

  为了寻找有用的抗爱滋病药物，已经研究了一系列1-（2,3-二脱氧-2-氟-β-D-thopenopentofuranosyl）pyrimidines的合成，化学，生物化学和抗HIV活性。通过2，3-二脱氧核糖中间体进行合成，该中间体通过在与尿嘧啶或胞嘧啶糖苷配子缩合之前而不是之后除去糖的3'-羟基来促进类似物的制备。2'-F-dd-尿苷类似物7a-d（在5位上具有H，F，Cl和CH3取代）以及4-脱氧化合物（12b）对感染了ATH8或CEM的细胞无保护作用HIV-1。在相应的胞苷系列中，5-氯类似物（11）没有活性。然而，2′-氟-2′，3′-二脱氧阿拉伯糖基胞嘧啶10a和其5-氟类似物10b都具有活性。虽然这两种化合物都不具有像ddC或5-F-ddC那样的强效作用（2b），但10b可以完全抵抗两种宿主细胞系中HIV的细胞病变作用。2'-氟取代赋予双脱氧核苷化学和酶稳定性。尽管双脱氧嘧啶核

  DOI：

  10.1021/jm00090a008
• 作为产物：
  描述：

  5-O-Benzoyl-2-deoxy-2-fluoro-1-O-methyl-β-D-arabinofuranose 在 偶氮二异丁腈 、 三正丁基氢锡 、 sodium hydride 作用下， 以 甲苯 为溶剂， 反应 4.33h， 生成 5-O-Benzoyl-2,3-dideoxy-2-fluoro-1-O-methyl-β-D-threo-pentofuranose
  参考文献：
  名称：

  Wysocki Jr.; Siddiqui; Barchi Jr., Synthesis, 1991, # 11, p. 1005 - 1008

  摘要：

  DOI：

文献信息

• 2'-fluorofuranosyl derivatives and novel method of preparing
  申请人：The United States of America as represented by the Department of Health

  公开号：US05336764A1

  公开（公告）日：1994-08-09

  A compound has the formula ##STR1## wherein R is selected from the group consisting of (C.sub.7 -C.sub.20)aroyl, (C.sub.6 -C.sub.20)aryl, aralkyl and alkylaryl, and (C.sub.1 -C.sub.10)alkyl-di(C.sub.6 -C.sub.20)aryl Si, R' is selected from the group consisting of (C.sub.1 -C.sub.10)alkyl, (C.sub.7 -C.sub.20)aroyl and (C.sub.2 -C.sub.12)acyl, all of which may be further substituted with O, S, N or alkyl, and R'" is selected from the group consisting of halogen, (C.sub.1 -C.sub.10)alkoxy, (C.sub.1 -C.sub.10)acyloxy, O-methane-sulfonyl and O-p-toluenesulfonyl. A composition of matter comprises 0.001 to 99.999 wt % of the above compound.

  一种化合物的分子式为##STR1##其中R从以下组中选择：(C.sub.7 -C.sub.20)芳酰基，(C.sub.6 -C.sub.20)芳基，芳基烷基和烷基芳基，以及(C.sub.1 -C.sub.10)烷基-二(C.sub.6 -C.sub.20)芳基Si，R'从以下组中选择：(C.sub.1 -C.sub.10)烷基，(C.sub.7 -C.sub.20)芳酰基和(C.sub.2 -C.sub.12)酰基，这些都可以进一步取代为O、S、N或烷基，R'"从以下组中选择：卤素，(C.sub.1 -C.sub.10)烷氧基，(C.sub.1 -C.sub.10)酰氧基，O-甲烷磺酰基和O-p-甲苯磺酰基。一种物质组合包括上述化合物的0.001至99.999重量百分比。
• Chemistry and Anti-HIV Activity of 2′-β-Fluoro-2′,3′-dideoxyguanosine
  作者：Harry Ford、John S. Driscoll、Maqbool Siddiqui、James A. Kelley、Hioraki Mitsuya、Takuma Shirasaka、David G. Johns、Victor E. Marquez

  DOI：10.1080/15257779408013236

  日期：1994.3

  The 2'-beta-fluoro analogue of 2',3'-dideoxyguanosine has been prepared by two synthetic routes. This compound and two analogues have anti-HIV activity in at least two of three host cell systems used (ATH8, CEM, PEL). These compounds, as well as their ddGuo parents, have been characterized with regard to their acid-stabilities, octanol-water partition coefficients, and enzyme substrate properties for adenosine deaminase and purine nucleoside phosphorylase. F-ddGuo analogues are less potent but more stable than their non-fluorinated parent compounds.
• The “β-Fluorine Effect” in the Non-Metal Hydride Radical Deoxygenation of Fluorine-Containing Nucleoside Xanthates
  作者：Maqbool A. Siddiqui、John S. Driscoll、Elie Abushanab、James A. Kelley、Joseph J. Barchi、Victor E. Marquez

  DOI：10.1080/15257770008032993

  日期：2000.1

  An alternative method to conduct a Barton-McCombie deoxygenation in nucleosides Is described. The utility of the procedure is limited to structures with an electronegative substituent, particularly fluorine, in the beta-position relative to the radical center. The process is radical in nature and triggered by peroxides. The abstraction of hydrogen from the solvent is favorably influenced by the presence of a beta-fluorine.