2,3,4-tri-O-para-nitrobenzoyl-α-L-fucopyranosyl bromide | 1330003-99-0

• 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: 2,3,4-tri-O-para-nitrobenzoyl-α-L-fucopyranosyl bromide
• CAS: 1330003-99-0
• 化学式: C₂₇H₂₀BrN₃O₁₃
• 分子量: 674.372
• InChiKey: AHOOUZRVJUFAEO-RREWDGISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.53
• 重原子数：
  44.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  217.55
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-para-nitrobenzoyl-α-L-fucopyranosyl bromide 、 甲基 6-O-[二甲基(2-甲基-2-丙基)硅烷基]-alpha-D-吡喃甘露糖苷 在 diphenylborate ethanolamine ester 、 silver(l) oxide 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以40%的产率得到methyl 3-O-(2,3,4-tri-O-para-nitrobenzoyl-β-L-fucopyranosyl)-α-D-mannopyranoside
  参考文献：
  名称：

  Regioselective Activation of Glycosyl Acceptors by a Diarylborinic Acid-Derived Catalyst

  摘要：

  A derivative of diphenylborinic add promotes catalytic, regioselective Koenigs-Knorr glycosylations of carbohydrate derivatives bearing multiple secondary hydroxyl groups. Robust levels of selectivity for the equatorial OH group of cis-1,2-diol motifs are demonstrated in reactions of seven acceptors derived from galactose, mannose, fucose, and arabinose using a variety of glycosyl halide donors. Catalyst control presents a new means of generating defined glycosidic linkages from unprotected or minimally protected carbohydrate feedstocks.

  DOI：

  10.1021/ja2062715
• 作为产物：
  描述：

  methyl-(2,3,4-tri-O-para-nitrobenzoyl)-α-L-fucopyranose 在 氢溴酸 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以14%的产率得到2,3,4-tri-O-para-nitrobenzoyl-α-L-fucopyranosyl bromide
  参考文献：
  名称：

  Regioselective Activation of Glycosyl Acceptors by a Diarylborinic Acid-Derived Catalyst

  摘要：

  A derivative of diphenylborinic add promotes catalytic, regioselective Koenigs-Knorr glycosylations of carbohydrate derivatives bearing multiple secondary hydroxyl groups. Robust levels of selectivity for the equatorial OH group of cis-1,2-diol motifs are demonstrated in reactions of seven acceptors derived from galactose, mannose, fucose, and arabinose using a variety of glycosyl halide donors. Catalyst control presents a new means of generating defined glycosidic linkages from unprotected or minimally protected carbohydrate feedstocks.

  DOI：

  10.1021/ja2062715