methyl 5-O-(N-acetyl-2,3-aziridino-5-O-benzoyl-2,3-dideoxy-α-D-ribofuranosyl)-2,3-anhydro-α-D-lyxofuranoside | 1431388-97-4

• 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: methyl 5-O-(N-acetyl-2,3-aziridino-5-O-benzoyl-2,3-dideoxy-α-D-ribofuranosyl)-2,3-anhydro-α-D-lyxofuranoside
• 英文别名: [(1S,2S,4S,5R)-6-acetyl-4-[[(1S,2R,4S,5S)-4-methoxy-3,6-dioxabicyclo[3.1.0]hexan-2-yl]methoxy]-3-oxa-6-azabicyclo[3.1.0]hexan-2-yl]methyl benzoate
• CAS: 1431388-97-4
• 化学式: C₂₀H₂₃NO₈
• 分子量: 405.405
• InChiKey: PDXUYSJVWPQDLZ-TWTVBBKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  95.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  N-acetyl-2,3-aziridino-5-O-benzoyl-2,3-dideoxy-d-ribofuranose 在 三氟甲磺酸三甲基硅酯 、 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 3.83h， 生成 methyl 5-O-(N-acetyl-2,3-aziridino-5-O-benzoyl-2,3-dideoxy-α-D-ribofuranosyl)-2,3-anhydro-α-D-lyxofuranoside 、 methyl 5-O-(N-acetyl-2,3-aziridino-5-O-benzoyl-2,3-dideoxy-β-D-ribofuranosyl)-2,3-anhydro-β-D-lyxofuranoside
  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

文献信息

• Glycosylations with 2,3-aziridinofuranose derivatives
  作者：Md Faiaz Ahmed、Todd L. Lowary

  DOI：10.1016/j.tet.2013.03.074

  日期：2013.5

  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.