2,2'-Anhydro-3'-deoxy-5'-O-(4-methoxyphenyl)-3'-methylidene-5-methyl-threo-pentofuranosyl-β-D-uracil | 141865-65-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,2'-Anhydro-3'-deoxy-5'-O-(4-methoxyphenyl)-3'-methylidene-5-methyl-threo-pentofuranosyl-β-D-uracil
• 英文别名: (2R,4S,6S)-4-[(4-methoxyphenoxy)methyl]-5-methylidene-3,7-dioxa-1,9-diazatricyclo[6.4.0.02,6]dodeca-8,11-dien-10-one
• CAS: 141865-65-8
• 化学式: C₁₇H₁₆N₂O₅
• 分子量: 328.324
• InChiKey: GKLRZKAHLDNVGT-VNQPRFMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  69.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2'-Anhydro-3'-deoxy-5'-O-(4-methoxyphenyl)-3'-methylidene-5-methyl-threo-pentofuranosyl-β-D-uracil 在 叠氮化锂 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以85%的产率得到3'-(Azidomethyl)-2',3'-didehydro-2',3'-dideoxy-5'-O-(4-methoxyphenyl)-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：

  2'-O-Acetyl-3'-deoxy-5'-O-(4-methoxyphenyl)-3'-methylidene-β-D-uridine 在 sodium methylate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 2,2'-Anhydro-3'-deoxy-5'-O-(4-methoxyphenyl)-3'-methylidene-5-methyl-threo-pentofuranosyl-β-D-uracil
  参考文献：
  名称：

  Synthesis of branched nucleosides closely related to AZT, involving SN2′ opening of anhydronucleosides.

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(00)60576-2

文献信息

• Synthesis of various 3'-branched 2',3'-unsaturated pyrimidine nucleosides as potential anti-HIV agents
  作者：S. Czernecki、A. Ezzitouni

  DOI：10.1021/jo00052a057

  日期：1992.12

  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.
• 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.