甲基2,3-二脱氧-3-氟-5-O-(4-苯基苯甲酰基)-α-D-赤型-呋喃戊糖苷 | 129468-51-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 甲基2,3-二脱氧-3-氟-5-O-(4-苯基苯甲酰基)-α-D-赤型-呋喃戊糖苷
• 英文名称: methyl 2,3-dideoxy-3-fluoro-5-O-(4-phenylbenzoyl)-β-D-erythro-pentofuranoside
• 英文别名: methyl 3-fluoro-2,3-dideoxy-5-O-(4-phenylbenzoyl)-β-D-erythro-pentofuranoside；2,3-dideoxy-3-fluoro-D-erythro-pentafuranoside；methyl 2,3-dideoxy-3-fluoro-5-O-(4-phenylbenzoyl)-beta-d-erythro-pentofuranoside；[(2R,3S,5R)-3-fluoro-5-methoxyoxolan-2-yl]methyl 4-phenylbenzoate
• CAS: 129468-51-5
• 化学式: C₁₉H₁₉FO₄
• 分子量: 330.356
• InChiKey: GPEUOGREWRRXPI-RCCFBDPRSA-N

物化性质

• 熔点：
  58-60℃
• 沸点：
  459.0±45.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 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：

  甲基2,3-二脱氧-3-氟-5-O-(4-苯基苯甲酰基)-α-D-赤型-呋喃戊糖苷 在 三氟甲磺酸三甲基硅酯 、 sodium methylate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 2.0h， 生成 1-(2,3-dideoxy-3-fluoro-β-D-erythro-pentofuranosyl)-5-isobutyrylamino-2,4(1H,3H)-pyrimidinedione
  参考文献：
  名称：

  Synthesis of 2′,3′-Dideoxy-3′-fluorouridines with Potential Anti-HIV Activity According to Neural Network Calculations

  摘要：

  以三氟甲磺酸三甲基硅酯为催化剂，将 2,3-二脱氧-3-氟-5-O-(4-苯基苯甲酰基)-δ-D-赤式戊呋喃糖苷与三甲基硅烷化的 5-取代尿嘧啶缩合，得到核苷。在 5-硝基尿嘧啶的情况下，分离出了一种无环核苷，据信它是相应核苷的中间体。 5 取代基是从对 HIV-1 有潜在活性的化合物的神经网络计算中选出的。缩合反应产生的所有化合物都在甲醇中用甲醇钠进行了脱乙酰处理。

  DOI：

  10.1055/s-1994-25515
• 作为产物：
  描述：

  methyl 2-deoxy-5-O-(4-phenylbenzoyl)-β-D-erythro-pentofuranoside 在 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 反应 120.0h， 以57%的产率得到甲基2,3-二脱氧-3-氟-5-O-(4-苯基苯甲酰基)-α-D-赤型-呋喃戊糖苷
  参考文献：
  名称：

  Abdel-Bary, Hamed M.; El-Barbary, Ahmed A.; Khodair, Ahmed I., Bulletin de la Societe Chimique de France, 1995, vol. 132, # 2, p. 149 - 155

  摘要：

  DOI：

文献信息

• Synthesis of 4-Methylthio Analogues of FLT and AZT and their Evaluation against HIV
  作者：Adel A.-H. Abdel-Rahman、Hamed M. Abdel-Bary、Erik B. Pedersen、Claus Nielsen

  DOI：10.1002/ardp.19953280112

  日期：——

  3′‐amino nucleoside. The 3′‐amino nucleoside was also obtained by condensation of 4‐methylthiothymidine with a 3‐phthalimido sugar 14 followed by deprotection. The 4‐methylthio analogue 11 of AZT showed moderate activity against HIV.

  甲硅烷基化的 4-甲基硫尿嘧啶和 4-甲基硫代胸腺嘧啶在 TMS 三氟甲磺酸酯存在下与甲基 2,3-双脱氧-3-氟-5-O-（4-苯基苯甲酰基）-D-赤型-戊呋喃糖苷（3）和甲基 3-缩合叠氮基-5-O-(叔丁基二苯基甲硅烷基)-2,3-双脱氧-D-赤型-五呋喃糖苷(8)，分别得到脱保护的相应核苷。3'-叠氮基核苷用三苯基膦还原成相应的 3'-氨基核苷。3'-氨基核苷也是通过 4-甲基硫代胸苷与 3-邻苯二甲酰亚胺糖 14 缩合然后脱保护获得的。AZT 的 4-甲硫基类似物 11 对 HIV 表现出中等活性。
• Synthesis of 3?-deoxy-3?-fluoro and -3?-amino nucleosides from 2-methylthiopyrimidin-4(1H)-ones
  作者：M. A. Zahran、A. E. -S. Abdel-Megied、A. A. -H. Abdel-Rahman、M. A. Sofan、C. Nielsen、E. B. Pedersen

  DOI：10.1007/bf00807039

  日期：——

  Methyl 2,3-dideoxy-3-fluoro-5-O-(4-phenylbenzoyl)-beta-D-erythro-pentofuranoside (3) as well as 1,5-di-O-acetyl-2,3-dideoxy-3-phthalimodo-beta-D-erythro-pentofuranose (12) were condensed with silylated 2-methylthiopyridin-4(1H)-ones 2a, b in the presence of trimethylsilyl triflate as a catalyst to produce the corresponding nucleosides 5, 6, 13. In these reactions, an endocyclic cleavage of C-O in 3 took place; therefore, acyclic nucleosides 4a,b were also formed. All 3'-fluoro nucleosides were deprotected with NH3/MeOH; the 3'-phthalimido nucleosides were deprotected with methylamine in ethanol. The latter method resulted in a concomitant substitution reaction in the pyrimidine moiety with replacement of the methylthio group. The 2-methylthio analogue of 3'-deoxy-3'-fluorothylmidine showed moderate activity against HIV-1.
• Synthesis of 5-dialkylaminomethyl-3′-azido and 3′-fluoro-2′,3′-dideoxyuridines for evaluation as anti-HIV agents
  作者：Mohammed S. Motawia、Per T. Jørgensen、Anni Larnkjær、Erik B. Pedersen、Claus Nielsen

  DOI：10.1007/bf00808509

  日期：1993.1

  Uracil (8) was substituted in a Mannich reaction to give the 5-substituted dialkylaminomethyluracils 11a-f in 65-85% yield. Compounds 11a-f were silylated with hexamethyldisilazane and coupled with 2,3-dideoxy-3-fluoro-D-erythro-pentofuranoside 4 and 3-azido-2,3-dideoxy-D-erythro-pentofuranoside 7 to give the corresponding 3'-fluoro-2',3'-dideoxynucleosides 13a-f and 3'-azido-2',3'-dideoxy nucleosides 16d,f, respectively, by using trimethylsilyl trifluoromethanesulfonate as a catalyst. Deprotection of the 5-O-(4-phenylbenzoyl) protected nucleosides 13a-f and 16d,f with saturated methanolic ammonia and separation by chromatography yielded the new derivatives of 2',3'-dideoxy-3'-fluorouridines 14a-f and 15a-f and 2',3'-dideoxy-3'-azidouridines 17d,f and 18d,f.
• El-Barbary, Ahmed A.; El-Brollosy, Nasser R.; Abdel-Bary, Hamed M., Liebigs Annalen, 1995, # 7, p. 1371 - 1376
  作者：El-Barbary, Ahmed A.、El-Brollosy, Nasser R.、Abdel-Bary, Hamed M.、Pedeson, Erik B.、Stein, Paul、Nielsen, Claus

  DOI：——

  日期：——
• A New Approach for Syntheses of 2′,3′-Dideoxy- 2′,3′-dehydronucleosides Using 2,2-Difluoro- 1,3-dimethylimidazolidine (DFI) as a Dehydrating Reagent
  作者：Hideki Umetani、Hiroshi Sonoda、Hironori Komatsu

  DOI：10.1081/ncn-120022607

  日期：2003.10

  We found that 2,2-difluoro-1,3-dimethylimidazolidine (DFI) is useful for not only fluorination but also dehydrating reactions. This dehydrating ability of DFI was applied to the syntheses of dihydrofurans (2) that are possible starting materials for various anticancer or antiviral drugs.