N-((R)-3-Benzyloxymethyl-5-hydroxy-tetrahydro-furan-3-yl)-acetamide | 478945-00-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-((R)-3-Benzyloxymethyl-5-hydroxy-tetrahydro-furan-3-yl)-acetamide
• 英文别名: N-[(3R)-5-hydroxy-3-(phenylmethoxymethyl)oxolan-3-yl]acetamide
• CAS: 478945-00-5
• 化学式: C₁₄H₁₉NO₄
• 分子量: 265.309
• InChiKey: YOZWZAFFMAWQLH-ARLHGKGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-((R)-3-Benzyloxymethyl-5-hydroxy-tetrahydro-furan-3-yl)-acetamide 在 氨 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 甲醇 为溶剂， 生成 N-[(3R,5R)-5-(6-Amino-4,5-dihydro-purin-9-yl)-3-benzyloxymethyl-tetrahydro-furan-3-yl]-acetamide
  参考文献：
  名称：

  Stereoselective synthesis of amino-substituted apio dideoxynucleosides through a distant neighboring group effect

  摘要：

  Novel amino-substituted apio nucleoside (2R,4R)-LJ-45 as a potential anti-HBV agent was stereoselectively synthesized from the known oxazolidine 1 through a distant neighboring group effect. It is believed that this synthetic method using a chiral template, (-)-L-serine methyl ester can be generally applied to the synthesis of other chiral amino-substituted nucleosides. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01295-9
• 作为产物：
  描述：

  (2R,4R)-4-Allyl-4-benzyloxymethyl-2-tert-butyl-oxazolidine-3-carbaldehyde 在 对甲苯磺酸 、 臭氧 、 胍 作用下， 以 吡啶 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 生成 N-((R)-3-Benzyloxymethyl-5-hydroxy-tetrahydro-furan-3-yl)-acetamide
  参考文献：
  名称：

  Stereoselective synthesis of amino-substituted apio dideoxynucleosides through a distant neighboring group effect

  摘要：

  Novel amino-substituted apio nucleoside (2R,4R)-LJ-45 as a potential anti-HBV agent was stereoselectively synthesized from the known oxazolidine 1 through a distant neighboring group effect. It is believed that this synthetic method using a chiral template, (-)-L-serine methyl ester can be generally applied to the synthesis of other chiral amino-substituted nucleosides. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01295-9