N-acetyl-2,3-aziridino-5-O-benzoyl-2,3-dideoxy-β-D-ribofuranosyl trichloroacetimidate | 1431388-87-2

• 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-acetyl-2,3-aziridino-5-O-benzoyl-2,3-dideoxy-β-D-ribofuranosyl trichloroacetimidate
• CAS: 1431388-87-2
• 化学式: C₁₆H₁₅Cl₃N₂O₅
• 分子量: 421.664
• InChiKey: GBSAJLPIACSRQA-SWXXGJRHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.53
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  88.69
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  辛醇 、 N-acetyl-2,3-aziridino-5-O-benzoyl-2,3-dideoxy-β-D-ribofuranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.58h， 以47.368%的产率得到
  参考文献：
  名称：

  Glycosylations with 2,3-aziridinofuranose derivatives

  摘要：

  Two aziridine-containing pentofuranose derivatives were synthesized from D-arabinose and their ability to glycosylate alcohols was explored. The major products are those in which the newly formed glycosidic bond is cis to the aziridine moiety, although in all cases the stereoselectivity is modest. The analogous epoxides have been shown to be more highly stereoselective glycosyl donors. Differences in glycosylation stereoselectivity between the epoxide and aziridine-containing substrates was proposed to arise from steric hindrance between the alcohol acceptor and the nitrogen protecting group in the aziridine substrates. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.03.074
• 作为产物：
  描述：

  N-acetyl-2,3-aziridino-5-O-benzoyl-2,3-dideoxy-d-ribofuranose 、 三氯乙腈 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 2.25h， 以98%的产率得到N-acetyl-2,3-aziridino-5-O-benzoyl-2,3-dideoxy-β-D-ribofuranosyl trichloroacetimidate
  参考文献：
  名称：

  Glycosylations with 2,3-aziridinofuranose derivatives

  摘要：

  Two aziridine-containing pentofuranose derivatives were synthesized from D-arabinose and their ability to glycosylate alcohols was explored. The major products are those in which the newly formed glycosidic bond is cis to the aziridine moiety, although in all cases the stereoselectivity is modest. The analogous epoxides have been shown to be more highly stereoselective glycosyl donors. Differences in glycosylation stereoselectivity between the epoxide and aziridine-containing substrates was proposed to arise from steric hindrance between the alcohol acceptor and the nitrogen protecting group in the aziridine substrates. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.03.074