1,2,3-tri-O-benzoyl-4-O-trifluoromethylsulfonyl-β-L-arabinopyranose | 82040-49-1

• 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: 1,2,3-tri-O-benzoyl-4-O-trifluoromethylsulfonyl-β-L-arabinopyranose
• 英文别名: 1,2,3-tri-O-benzoyl-4-O-trifluoromethanesulphonyl-β-L-arabinopyranose；[(2R,3R,4R,5S)-2,3-dibenzoyloxy-5-(trifluoromethylsulfonyloxy)oxan-4-yl] benzoate
• CAS: 82040-49-1
• 化学式: C₂₇H₂₁F₃O₁₀S
• 分子量: 594.519
• InChiKey: SAASZLFWPYJLTD-BTKWVRSESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  41
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  140
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  1,2,3-tri-O-benzoyl-4-O-trifluoromethylsulfonyl-β-L-arabinopyranose 在 sodium methylate 、 sodium 作用下， 以 甲醇 为溶剂， 反应 20.0h， 生成 4-S-β-D-xylopyranosyl-4-thio-α-D-xylopyranose
  参考文献：
  名称：

  不可代谢的诱导剂诱导木霉木霉中的d-木聚糖降解酶。4-硫代木糖的合成

  摘要：

  摘要木糖木霉的d-木聚糖降解酶可以被多种寡糖和多糖诱导。当1-阿拉伯-d-木聚糖用作碳源时，诱导是最佳的。该酶也是由在4-硫代木糖（4-S-β-d-木吡喃糖基-4-硫代-d-木吡喃糖）和甲基β-d-木吡喃糖苷存在下在甘油上生长的细胞产生的。这些诱导物未被细胞吸收。然而，诱导程度低于木二糖。1,2,3-三-O-苯甲酰基-4-O-三氟甲基磺酰基-β-1-阿糖基吡喃糖与1-硫代-β-钠盐的反应得到硫代叶酰糖，总产率为55-60％。在N′，N″，N′-六甲基磷酰胺中的d-吡喃木糖，然后将所得的4-硫代二糖进行O-脱酰。

  DOI：

  10.1016/0008-6215(85)90013-8
• 作为产物：
  描述：

  L-(+)-arabinose 在 吡啶 、 水 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.92h， 生成 1,2,3-tri-O-benzoyl-4-O-trifluoromethylsulfonyl-β-L-arabinopyranose
  参考文献：
  名称：

  Stereoselective synthesis of thioxylooligosaccharides from S-glycosyl isothiourea precursors

  摘要：

  A stereoselective synthesis of thioxylo-di-, -tri-, -tetra- and -penta-saccharides from S-glycosyl isothiourea precursors is described. The synthesis was performed starting from 2,3,4-tri-O-acetyl-beta -D-xylopyranosyl isothiouronium bromide using a triethylamine promoted reaction with 1,2,3-tri-O-benzoyl-4-O-lrifluoromethanesuIphonyl-beta -L-arabinopyranose. The resulting 4-thioxylobisse was then converted into the corresponding isothiouroniurn bromide and used for the synthesis of 4,4 ' -dithioxylotriose. Higher homologues of the series and their alpha -methyl glycosides were also prepared. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00775-4

文献信息

• Stereoselective synthesis of thioxylooligosaccharides from S-glycosyl isothiourea precursors
  作者：Farid M Ibatullin、Konstantin A Shabalin、Janne V Jänis、Stanislav I Selivanov

  DOI：10.1016/s0040-4039(01)00775-4

  日期：2001.7

  A stereoselective synthesis of thioxylo-di-, -tri-, -tetra- and -penta-saccharides from S-glycosyl isothiourea precursors is described. The synthesis was performed starting from 2,3,4-tri-O-acetyl-beta -D-xylopyranosyl isothiouronium bromide using a triethylamine promoted reaction with 1,2,3-tri-O-benzoyl-4-O-lrifluoromethanesuIphonyl-beta -L-arabinopyranose. The resulting 4-thioxylobisse was then converted into the corresponding isothiouroniurn bromide and used for the synthesis of 4,4 ' -dithioxylotriose. Higher homologues of the series and their alpha -methyl glycosides were also prepared. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Induction of d-xylan-degrading enzymes in Trichoderma lignorum by nonmetabolizable inducers. A synthesis of 4-thioxylobiose
  作者：Jacques Defaye、Hugues Driguez、Michael John、Jürgen Schmidt、Eric Ohleyer

  DOI：10.1016/0008-6215(85)90013-8

  日期：1985.6

  The d -xylan-degrading enzymes of Trichoderma lignorum can be induced by several oligo- and poly-saccharides. The induction is optimal when l -arabino- d -xylan is used as carbon source. The enzymes were also produced by cells grown on glycerol in the presence of 4-thioxylobiose (4- S -β- d -xylopyranosyl-4-thio- d -xylopyranose) and methyl β- d -xylopyranoside. These inducers were not taken up by the

  摘要木糖木霉的d-木聚糖降解酶可以被多种寡糖和多糖诱导。当1-阿拉伯-d-木聚糖用作碳源时，诱导是最佳的。该酶也是由在4-硫代木糖（4-S-β-d-木吡喃糖基-4-硫代-d-木吡喃糖）和甲基β-d-木吡喃糖苷存在下在甘油上生长的细胞产生的。这些诱导物未被细胞吸收。然而，诱导程度低于木二糖。1,2,3-三-O-苯甲酰基-4-O-三氟甲基磺酰基-β-1-阿糖基吡喃糖与1-硫代-β-钠盐的反应得到硫代叶酰糖，总产率为55-60％。在N′，N″，N′-六甲基磷酰胺中的d-吡喃木糖，然后将所得的4-硫代二糖进行O-脱酰。