1″,5″-dideoxy-2″,3″-O-isopentylidene-5″-phthalimido-1″-[2′,3′-O-isopropylidene-5′(S)-ethynyl-uridinyl]-β-D-ribofuranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1″,5″-dideoxy-2″,3″-O-isopentylidene-5″-phthalimido-1″-[2′,3′-O-isopropylidene-5′(S)-ethynyl-uridinyl]-β-D-ribofuranose
• 英文别名: 2-[[(3aR,4R,6R,6aR)-4-[(1S)-1-[(3aR,4R,6R,6aR)-4-(2,4-dioxopyrimidin-1-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]prop-2-ynoxy]-2,2-diethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl]isoindole-1,3-dione
• 化学式: C₃₂H₃₅N₃O₁₁
• 分子量: 637.643
• InChiKey: ARHKDKAQNPVERD-IAIMGBIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  46
• 可旋转键数：
  8
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  151
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1″,5″-dideoxy-2″,3″-O-isopentylidene-5″-phthalimido-1″-[2′,3′-O-isopropylidene-5′(S)-ethynyl-uridinyl]-β-D-ribofuranose 在 copper(II) sulfate 、 sodium ascorbate 、 N,N-二异丙基乙胺 、 甲胺 作用下， 以 甲醇 、 乙醇 、 水 、 叔丁醇 为溶剂， 反应 23.0h， 生成
  参考文献：
  名称：

  Toward Analogues of MraY Natural Inhibitors: Synthesis of 5′-Triazole-Substituted-Aminoribosyl Uridines Through a Cu-Catalyzed Azide–Alkyne Cycloaddition

  摘要：

  A straightforward strategy for the synthesis of triazole-containing MraY inhibitors has been developed. It involves the sequential introduction of a terminal alkyne at the S' position of an uridine derivative and O-glycosylation with a protected aminoribose leading to an elaborated alkyne scaffold. An efficient Cu (1)-catalyzed azide-alkyne cycloaddition (CuAAC) allowed the introduction of chemical diversity toward a small library of inhibitors.

  DOI：

  10.1021/jo4014035
• 作为产物：
  描述：

  1-[6,7-dideoxy-2,3-O-isopropylidene-7-C-(triethylsilyl)-β-D-allo-hept-6-ynofuranosyl]uracil 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 、 1″,5″-dideoxy-2″,3″-O-isopentylidene-5″-phthalimido-1″-[2′,3′-O-isopropylidene-5′(S)-ethynyl-uridinyl]-β-D-ribofuranose
  参考文献：
  名称：

  Toward Analogues of MraY Natural Inhibitors: Synthesis of 5′-Triazole-Substituted-Aminoribosyl Uridines Through a Cu-Catalyzed Azide–Alkyne Cycloaddition

  摘要：

  A straightforward strategy for the synthesis of triazole-containing MraY inhibitors has been developed. It involves the sequential introduction of a terminal alkyne at the S' position of an uridine derivative and O-glycosylation with a protected aminoribose leading to an elaborated alkyne scaffold. An efficient Cu (1)-catalyzed azide-alkyne cycloaddition (CuAAC) allowed the introduction of chemical diversity toward a small library of inhibitors.

  DOI：

  10.1021/jo4014035

文献信息

• Toward Analogues of MraY Natural Inhibitors: Synthesis of 5′-Triazole-Substituted-Aminoribosyl Uridines Through a Cu-Catalyzed Azide–Alkyne Cycloaddition
  作者：Mickaël J. Fer、Samir Olatunji、Ahmed Bouhss、Sandrine Calvet-Vitale、Christine Gravier-Pelletier

  DOI：10.1021/jo4014035

  日期：2013.10.18

  A straightforward strategy for the synthesis of triazole-containing MraY inhibitors has been developed. It involves the sequential introduction of a terminal alkyne at the S' position of an uridine derivative and O-glycosylation with a protected aminoribose leading to an elaborated alkyne scaffold. An efficient Cu (1)-catalyzed azide-alkyne cycloaddition (CuAAC) allowed the introduction of chemical diversity toward a small library of inhibitors.