dibenzylphosphoryl 2,3,4-tri-O-benzoyl-6-deoxy-6-fluoro-β-L-galactopyranoside | 303069-75-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dibenzylphosphoryl 2,3,4-tri-O-benzoyl-6-deoxy-6-fluoro-β-L-galactopyranoside
• CAS: 303069-75-2
• 化学式: C₄₁H₃₆FO₁₁P
• 分子量: 754.702
• InChiKey: SJODGQJJQTYOCV-ALIMGCNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.92
• 重原子数：
  54.0
• 可旋转键数：
  15.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  132.89
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  dibenzylphosphoryl 2,3,4-tri-O-benzoyl-6-deoxy-6-fluoro-β-L-galactopyranoside 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以95%的产率得到di(trimethylammonium)phosphoryl-2,3,4-tri-O-benzoyl-6-deoxy-6-fluoro-β-L-fucopyranoside
  参考文献：
  名称：

  Chemo-enzymatic synthesis of fluorinated sugar nucleotide: useful mechanistic Probes for glycosyltransferases

  摘要：

  An effective procedure for the synthesis of 2-deoxy-2-fluoro-sugar nucleotides via Selectfluor-mediated electrophilic fluorination of glycals with concurrent nucleophilic addition or chemo-enzymatic transformation has been developed. and the fluorinated sugar nucleotides have been used as probes For glycosyltransferases, including fucosyltransferase III, V, VI, and VII, and sialyl transferases. In general, these fluorinated sugar nuclceotides act as competitive inhibitors versus sugar nucleotide substrates and form a tight complex with the glycosyltransferase. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00139-5
• 作为产物：
  描述：

  L-galactose 在 2,3,5-三甲基吡啶 、 硫酸 、 氢溴酸 、 copper(II) sulfate 、 溶剂黄146 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 吡啶 、 二氯甲烷 、 水 为溶剂， 反应 64.0h， 生成 dibenzylphosphoryl 2,3,4-tri-O-benzoyl-6-deoxy-6-fluoro-β-L-galactopyranoside
  参考文献：
  名称：

  Chemo-enzymatic synthesis of fluorinated sugar nucleotide: useful mechanistic Probes for glycosyltransferases

  摘要：

  An effective procedure for the synthesis of 2-deoxy-2-fluoro-sugar nucleotides via Selectfluor-mediated electrophilic fluorination of glycals with concurrent nucleophilic addition or chemo-enzymatic transformation has been developed. and the fluorinated sugar nucleotides have been used as probes For glycosyltransferases, including fucosyltransferase III, V, VI, and VII, and sialyl transferases. In general, these fluorinated sugar nuclceotides act as competitive inhibitors versus sugar nucleotide substrates and form a tight complex with the glycosyltransferase. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00139-5