甲基2-脱氧-ALPHA-D-赤式-呋喃戊糖苷5-[1,1'-联苯]-4-羧酸酯 | 125611-96-3

• 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-脱氧-ALPHA-D-赤式-呋喃戊糖苷5-[1,1'-联苯]-4-羧酸酯
• 英文名称: Methyl 2-Deoxy-3-O-(methylsulfonyl)-5-O-(4-phenylbenzoyl)-α-D-erythro-pentofuranoside
• 英文别名: methyl 2-deoxy-5-O-(4-phenylbenzoyl)-α-D-erythro-pentofuranoside；((2R,3S,5S)-3-Hydroxy-5-methoxytetrahydrofuran-2-yl)methyl [1,1'-biphenyl]-4-carboxylate；[(2R,3S,5S)-3-hydroxy-5-methoxyoxolan-2-yl]methyl 4-phenylbenzoate
• CAS: 125611-96-3
• 化学式: C₁₉H₂₀O₅
• 分子量: 328.365
• InChiKey: CSLRIDAGGSABHP-KSZLIROESA-N

物化性质

• 沸点：
  511.6±50.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 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：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  甲基2-脱氧-ALPHA-D-赤式-呋喃戊糖苷5-[1,1'-联苯]-4-羧酸酯 在 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三氟甲磺酸三甲基硅酯 、 氨 、 三正丁基氢锡 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 27.5h， 生成 2,3-二脱氧胞啶
  参考文献：
  名称：

  Motawia, Mohammed S.; Pedersen, Erik B., Liebigs Annalen der Chemie, 1990, # 6, p. 599 - 602

  摘要：

  DOI：
• 作为产物：
  描述：

  2-deoxy-D-ribose 在 吡啶 、 盐酸 作用下， 反应 4.25h， 生成 甲基2-脱氧-ALPHA-D-赤式-呋喃戊糖苷5-[1,1'-联苯]-4-羧酸酯
  参考文献：
  名称：

  Motawia, Mohammed S.; Pedersen, Erik B., Liebigs Annalen der Chemie, 1990, # 6, p. 599 - 602

  摘要：

  DOI：

文献信息

• Convergent synthesis of 2′,3′-dideoxy-3′-methylthio and 2′,3′-dideoxy-3′-mercapto nucleosides and their disulfide analogues — Potential anti-HIV agents
  作者：Kim L. Dueholm、Youssef L. Aly、Per T. Jørgensen、Ahmed A. El-Barbary、Erik B. Pedersen、Claus Nielsen

  DOI：10.1007/bf00808508

  日期：1993.1

  The iodide 4(alpha) or 7 synthesized in three steps from 2-deoxy-D-ribose 1, has been subjected to a number of nucleophilic substitution reactions producing the 3-benzoylthio-, 3-methylthio- and the 3-thiocyanato-2,3-dideoxy-D-erythro-pentofuranosides 8,13 and 15, respectively, in addition to the disulfide 17 of their 3-mercapto analogue. Subjecting the thiobenzoate 8 to the Friedel-Crafts catalyzed silyl Hilbert Johnson reaction in conjunction with the silylated nucleobases of uracil, thymine and N4-isobutyrylcytosine 9a-c resulted in the isolation of the 2',3'-dideoxy-3'-mercapto nucleosides 11 and their disulfides 12 subsequent to deprotection. The 2,3-dideoxy-3-methylthio-pentofuranoside 13 afforded both anomers of the 2',3'-dideoxy-3'-methylthio nucleosides 19 and 20 under similar conditions. The first known example of a coupling directly on a 2,3-didehydro-2,3-dideoxyfuranose is presented. 2',3'-Dideoxy-3'-mercaptocytidine showed protection against HIV-1 in MT-4 cells with ED50 = 20 muM.
• 2-Deoxy-3-C-(hydroxymethyl)-D-pentofuranose Derivatives: Stereoselective Synthesis and Conversion into a Novel Class of Nucleoside Analogs
  作者：Claus Scheuer-Larsen、Henrik M. Pfundheller、Jesper Wengel

  DOI：10.1021/jo00127a041

  日期：1995.11

  Oxidation of pure anomers of 5-O-monoprotected methyl 2-deoxy-D-ribofuranosides 3-6 followed by Lombardo methylenation afforded the novel 3-C-methylene pentofuranosides 11-14. Subsequent osmium tetraoxide-catalyzed dihydroxylations of 11, 13, and 14 afforded a mixture of erythro- and three-configured S-C-hydroxymethyl furanosides 15/16, 18/19, and 20/21, respectively. However, analogous dihydroxylation of 5-O-(4-phenylbenzoyl)-protected beta-anomer 12 proceeded with complete stereoselectivity to give 3-C-(hydroxymethyl)-beta-D-erythro pentofuranoside 17 in 76% yield. Conversion of 17 to the corresponding primary tosylate 22, followed by base-catalyzed nucleophilic attack by the nucleobases adenine and thymine, afforded after deprotection compounds 25 and 26, respectively, as the first examples of a novel class of nucleoside analogues.
• Motawia, Mohammed S.; Pedersen, Erik B., Liebigs Annalen der Chemie, 1990, # 11, p. 1137 - 1139
  作者：Motawia, Mohammed S.、Pedersen, Erik B.

  DOI：——

  日期：——
• 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
  作者：Abdel-Bary, Hamed M.、El-Barbary, Ahmed A.、Khodair, Ahmed I.、Megied, Ahmed Es Abdel、Pedersen, Erik B.、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.