2-chloroethyl 2-O-benzoyl-3,5-di-O-(3,5-di-O-benzoyl-2-O-chloroacetyl-α-D-arabinofuranosyl)-α-D-arabinofuranoside | 1289100-91-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-chloroethyl 2-O-benzoyl-3,5-di-O-(3,5-di-O-benzoyl-2-O-chloroacetyl-α-D-arabinofuranosyl)-α-D-arabinofuranoside
• 英文别名: [(2R,3R,4S,5S)-3-benzoyloxy-5-[[(2R,3R,4S,5S)-4-benzoyloxy-3-[(2R,3S,4R,5R)-4-benzoyloxy-5-(benzoyloxymethyl)-3-(2-chloroacetyl)oxyoxolan-2-yl]oxy-5-(2-chloroethoxy)oxolan-2-yl]methoxy]-4-(2-chloroacetyl)oxyoxolan-2-yl]methyl benzoate
• CAS: 1289100-91-9
• 化学式: C₅₆H₅₁Cl₃O₂₀
• 分子量: 1150.37
• InChiKey: YNNBIAFUDBEHSQ-GEGNREEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  79
• 可旋转键数：
  31
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  240
• 氢给体数：
  0
• 氢受体数：
  20

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以71%的产率得到2-chloroethyl 2-O-benzoyl-3,5-di-O-(3,5-di-O-benzoyl-2-O-chloroacetyl-α-D-arabinofuranosyl)-α-D-arabinofuranoside
  参考文献：
  名称：

  Formation of orthoester-linked d-arabinofuranose oligosaccharides and their isomerization into the corresponding glycosides

  摘要：

  Orthoester-linked D-arabinofuranose oligosaccharides were isolated in high yield for the first time via glycosylations with 2-O-chloroacetyl-substituded D-arabinofuranose thioglycosides promoted by NIS-AgOTf in the presence of 4 A molecular sieves in CH2Cl2. These orthoesters can be rearranged into the isomeric glycosidically-linked oligosaccharides by treatment with TMSOTf in CH2Cl2, or in situ by extension of the reaction time. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.02.019

文献信息

• Formation of orthoester-linked d-arabinofuranose oligosaccharides and their isomerization into the corresponding glycosides
  作者：Polina I. Abronina、Sergey L. Sedinkin、Nikita M. Podvalnyy、Ksenia G. Fedina、Alexander I. Zinin、Vladimir I. Torgov、Leonid O. Kononov

  DOI：10.1016/j.tetlet.2011.02.019

  日期：2011.4

  Orthoester-linked D-arabinofuranose oligosaccharides were isolated in high yield for the first time via glycosylations with 2-O-chloroacetyl-substituded D-arabinofuranose thioglycosides promoted by NIS-AgOTf in the presence of 4 A molecular sieves in CH2Cl2. These orthoesters can be rearranged into the isomeric glycosidically-linked oligosaccharides by treatment with TMSOTf in CH2Cl2, or in situ by extension of the reaction time. (C) 2011 Elsevier Ltd. All rights reserved.
• 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.