2-chloroethyl 2-O-benzoyl-3,5-di-O-(3,5-di-O-benzoyl-α-D-arabinofuranosyl)-α-D-arabinofuranoside | 1392213-72-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-chloroethyl 2-O-benzoyl-3,5-di-O-(3,5-di-O-benzoyl-α-D-arabinofuranosyl)-α-D-arabinofuranoside
• 英文别名: [(2R,3S,4S,5S)-3-benzoyloxy-5-[[(2R,3R,4S,5S)-4-benzoyloxy-3-[(2R,3S,4S,5R)-4-benzoyloxy-5-(benzoyloxymethyl)-3-hydroxyoxolan-2-yl]oxy-5-(2-chloroethoxy)oxolan-2-yl]methoxy]-4-hydroxyoxolan-2-yl]methyl benzoate
• CAS: 1392213-72-7
• 化学式: C₅₂H₄₉ClO₁₈
• 分子量: 997.403
• InChiKey: MUGRTSQSJUUPGF-UITLZDKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  71
• 可旋转键数：
  25
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  227
• 氢给体数：
  2
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  phenyl 3,5-di-O-(di-tert-butylsilylene)-2-O-triisopropylsilyl-1-thio-α-D-arabinofuranoside 、 2-chloroethyl 2-O-benzoyl-3,5-di-O-(3,5-di-O-benzoyl-α-D-arabinofuranosyl)-α-D-arabinofuranoside 在 N-碘代丁二酰亚胺 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 17.67h， 以77%的产率得到2-chloroethyl 2-O-benzoyl-3,5-di-O-{3,5-di-O-benzoyl-2-O-[3,5-di-(tert-butylsilylene)-2-O-triisopropylsilyl-D-arabinofuranosyl]-α-D-arabinofuranosyl}-α-D-arabinofuranoside
  参考文献：
  名称：

  Synthesis of branched arabinofuranose pentasaccharide fragment of mycobacterial arabinans as 2-azidoethyl glycoside

  摘要：

  Branched arabinofuranose pentasaccharide with 2-azidoethyl aglycon was prepared for the first time by [3+1+1] bis-(1,2-cis)-glycosylation of trisaccharide diol with silyl-protected thioglycoside glycosyl donor. The presence of 2-azidoethyl aglycon would enable the preparation of neoglycoconjugates using the click chemistry approaches. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.05.021
• 作为产物：
  描述：

  2-chloroethyl 2-O-benzoyl-3,5-di-O-(3,5-di-O-benzoyl-2-O-chloroacetyl-α-D-arabinofuranosyl)-α-D-arabinofuranoside 在 水 作用下， 以 吡啶 为溶剂， 反应 1.0h， 以96%的产率得到2-chloroethyl 2-O-benzoyl-3,5-di-O-(3,5-di-O-benzoyl-α-D-arabinofuranosyl)-α-D-arabinofuranoside
  参考文献：
  名称：

  Synthesis of branched arabinofuranose pentasaccharide fragment of mycobacterial arabinans as 2-azidoethyl glycoside

  摘要：

  Branched arabinofuranose pentasaccharide with 2-azidoethyl aglycon was prepared for the first time by [3+1+1] bis-(1,2-cis)-glycosylation of trisaccharide diol with silyl-protected thioglycoside glycosyl donor. The presence of 2-azidoethyl aglycon would enable the preparation of neoglycoconjugates using the click chemistry approaches. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.05.021

文献信息

• Synthesis of branched arabinofuranose pentasaccharide fragment of mycobacterial arabinans as 2-azidoethyl glycoside
  作者：Ksenia G. Fedina、Polina I. Abronina、Nikita M. Podvalnyy、Nikolay N. Kondakov、Alexander O. Chizhov、Vladimir I. Torgov、Leonid O. Kononov

  DOI：10.1016/j.carres.2012.05.021

  日期：2012.8

  Branched arabinofuranose pentasaccharide with 2-azidoethyl aglycon was prepared for the first time by [3+1+1] bis-(1,2-cis)-glycosylation of trisaccharide diol with silyl-protected thioglycoside glycosyl donor. The presence of 2-azidoethyl aglycon would enable the preparation of neoglycoconjugates using the click chemistry approaches. (C) 2012 Elsevier Ltd. All rights reserved.