ethyl 3,5-di-O-benzoyl-2-O-chloroacetyl-1-thio-α-D-arabinofuranoside | 1289100-83-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 3,5-di-O-benzoyl-2-O-chloroacetyl-1-thio-α-D-arabinofuranoside
• 英文别名: [(2R,3R,4S,5R)-3-benzoyloxy-4-(2-chloroacetyl)oxy-5-ethylsulfanyloxolan-2-yl]methyl benzoate
• CAS: 1289100-83-9
• 化学式: C₂₃H₂₃ClO₇S
• 分子量: 478.95
• InChiKey: PKJADYKJNFRSKU-OYWYANMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl 3,5-di-O-benzoyl-2-O-chloroacetyl-1-thio-α-D-arabinofuranoside 、 [(2R,3R,4S,5S)-4-benzoyloxy-2-[[(2S,3S,4R,5R)-3-benzoyloxy-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-5-(2-chloroethoxy)oxolan-3-yl] benzoate 在 N-碘代丁二酰亚胺 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到
  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.