phenyl 3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-6-O-toluenesulfonyl-1-thio-α-D-mannopyranoside | 876862-54-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-6-O-toluenesulfonyl-1-thio-α-D-mannopyranoside
• CAS: 876862-54-3
• 化学式: C₂₅H₃₂O₉S₂
• 分子量: 540.656
• InChiKey: LLBDSNOVBIATMK-UJDVVMIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.09
• 重原子数：
  36.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  109.75
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  phenyl 3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-6-O-toluenesulfonyl-1-thio-α-D-mannopyranoside 在 sodium azide 、 potassium iodide 、 silver(l) oxide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 103.0h， 生成 6-azido-2,6-dideoxy-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-2-phenylthio-α-D-glucopyranosyl azide
  参考文献：
  名称：

  Synthesis of 2‐Deoxy‐2‐thiophenylglucosyl Azides through 1,2 Thio Migration of Thiophenyl Mannosides

  摘要：

  2-Deoxy-2-thio glucosyl azides bearing or not bearing an azido group at the 6-position can be conveniently obtained through a 1,2-thio migration from thiophenyl mannoside derivatives.

  DOI：

  10.1080/07328300500409150
• 作为产物：
  描述：

  对甲苯磺酰氯 、 phenyl 3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-diyl]-1-thio-α-D-mannopyranoside 在 四甲基乙二胺 作用下， 以 乙腈 为溶剂， 反应 1.5h， 以97%的产率得到phenyl 3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-6-O-toluenesulfonyl-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of 2‐Deoxy‐2‐thiophenylglucosyl Azides through 1,2 Thio Migration of Thiophenyl Mannosides

  摘要：

  2-Deoxy-2-thio glucosyl azides bearing or not bearing an azido group at the 6-position can be conveniently obtained through a 1,2-thio migration from thiophenyl mannoside derivatives.

  DOI：

  10.1080/07328300500409150

文献信息

• ‘Click chemistry’ in CuI-zeolites: a convenient access to glycoconjugates
  作者：Aurélien Alix、Stefan Chassaing、Patrick Pale、Jean Sommer

  DOI：10.1016/j.tet.2008.06.086

  日期：2008.9

  Zeolites modified with Cu-I ions are efficient catalyst for 'click' reactions involving carbohydrates and aminoacid derivatives. Glycopeptides and oligosaccharides mimics as well as multivalent carbohydrate derivatives have been obtained in good to high yield using heterogeneous Cu-I-modified zeolite catalysts. Contrarily to expectation, pore sizes and internal shapes within zeolites were not a limitation and large glucosyl ditriazoles, disaccharide triazoles, and glucosylated triazolylaminoacids could easily be obtained. Such Cu-I-zeolite heterogeneous catalysts greatly facilitated products recovery, through an easy filtration-solvent evaporation sequence, thus offering a convenient alternative to current methods. (C) 2008 Elsevier Ltd. All rights reserved.