2'-O-Acetyl-3'-deoxy-5'-O-(4-methoxyphenyl)-3'-methylidene-β-D-uridine | 141865-60-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2'-O-Acetyl-3'-deoxy-5'-O-(4-methoxyphenyl)-3'-methylidene-β-D-uridine
• 英文别名: [(2R,3R,5S)-2-(2,4-dioxopyrimidin-1-yl)-5-[(4-methoxyphenoxy)methyl]-4-methylideneoxolan-3-yl] acetate
• CAS: 141865-60-3
• 化学式: C₁₉H₂₀N₂O₇
• 分子量: 388.377
• InChiKey: VWJQNNFFFSHJCK-KBAYOESNSA-N

物化性质

• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.01
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  108.85
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2'-O-Acetyl-3'-deoxy-5'-O-(4-methoxyphenyl)-3'-methylidene-β-D-uridine 在 potassium cyanide 、 叠氮化锂 、 ammonium cerium(IV) nitrate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 15.5h， 生成 3'-(Azidomethyl)-2',3'-didehydro-2',3'-dideoxy-β-D-uridine
  参考文献：
  名称：

  Synthesis of various 3'-branched 2',3'-unsaturated pyrimidine nucleosides as potential anti-HIV agents

  摘要：

  A series of four new 2',3'-dideoxypyrimidine nucleosides was synthesized and their activity against HIV was evaluated. Coupling of a suitably protected 3-methylidene xylofuranose derivative 5 with thymine and uracil afforded branched nucleosides 7a and 7b. The latter was transformed into 2',3'-dideoxy-2',3'-didehydro 3'-branched nucleoside 1 by Barton deoxygenation during which an allylic rearrangement occurred. Compounds 7a and 7b were converted into the corresponding 2,2'-anhydro derivatives by an intramolecular Mitsunobu reaction. Treatment of these compounds with LiN3 in DMF afforded the branched azidonucleosides by S(N)2' reaction. Palladium-catalyzed azidation of the allylic ester 6a allowed the introduction of an azido group in a highly regio- and stereoselective manner at C-2', affording 12. The p-anisyl group employed for the protection of the primary hydroxyl of 5 was stable in acidic and basic conditions, allowing its removal only at the end of the synthesis.

  DOI：

  10.1021/jo00052a057
• 作为产物：
  描述：

  1,2-Di-O-Acetyl-3-deoxy-5-O-(4-methoxyphenyl)-3-methylidene-D-erythro-pentofuranose 、 尿嘧啶 在 三甲基氯硅烷 、 三氟甲磺酸三甲基硅酯 、 六甲基二硅氮烷 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.0h， 以70%的产率得到2'-O-Acetyl-3'-deoxy-5'-O-(4-methoxyphenyl)-3'-methylidene-β-D-uridine
  参考文献：
  名称：

  Synthesis of various 3'-branched 2',3'-unsaturated pyrimidine nucleosides as potential anti-HIV agents

  摘要：

  A series of four new 2',3'-dideoxypyrimidine nucleosides was synthesized and their activity against HIV was evaluated. Coupling of a suitably protected 3-methylidene xylofuranose derivative 5 with thymine and uracil afforded branched nucleosides 7a and 7b. The latter was transformed into 2',3'-dideoxy-2',3'-didehydro 3'-branched nucleoside 1 by Barton deoxygenation during which an allylic rearrangement occurred. Compounds 7a and 7b were converted into the corresponding 2,2'-anhydro derivatives by an intramolecular Mitsunobu reaction. Treatment of these compounds with LiN3 in DMF afforded the branched azidonucleosides by S(N)2' reaction. Palladium-catalyzed azidation of the allylic ester 6a allowed the introduction of an azido group in a highly regio- and stereoselective manner at C-2', affording 12. The p-anisyl group employed for the protection of the primary hydroxyl of 5 was stable in acidic and basic conditions, allowing its removal only at the end of the synthesis.

  DOI：

  10.1021/jo00052a057

文献信息

• Synthesis of branched nucleosides closely related to AZT, involving SN2′ opening of anhydronucleosides.
  作者：Stanislas Czernecki、Abdallah Ezzitouni

  DOI：10.1016/s0040-4039(00)60576-2

  日期：1993.1

  Three 2',3'-unsaturated pyrimidine nucleosides, bearing an azido-methyl group at 2' or 3' were synthesized as potential anti-HIV agents. The key step involves an SN2' opening of 2,2' or 2,3'-anhydronucleosides by azide ion.