[(2R,3R,4S,5S,6R)-2-azido-3-benzoyloxy-5-hydroxy-6-(phenylmethoxymethyl)oxan-4-yl] benzoate | 566199-64-2

• 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: [(2R,3R,4S,5S,6R)-2-azido-3-benzoyloxy-5-hydroxy-6-(phenylmethoxymethyl)oxan-4-yl] benzoate
• CAS: 566199-64-2
• 化学式: C₂₇H₂₅N₃O₇
• 分子量: 503.511
• InChiKey: DHVGDGXQVNMAKO-ZLOLNMDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4S,5S,6R)-2-azido-3-benzoyloxy-5-hydroxy-6-(phenylmethoxymethyl)oxan-4-yl] benzoate 在 甲醇 、 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 MS-AW₃₀₀ 、 sodium methylate 、 sodium hydride 、 三氟乙酸 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 Bn(-3)[Bn(-4)][Bn(-6)]Gal(a1-4)[Bn(-2)][Bn(-3)][Bn(-6)]Gal(b)-N3
  参考文献：
  名称：

  A galabiose-based two-dimensional scaffold for the synthesis of inhibitors targeting Pk- and P-antigen binding proteins

  摘要：

  A disaccharide scaffold based on galabiose (Galal-4Gal) was synthesized. Four different acceptors were evaluated in the alpha-galactosylation and a relationship between the nucleophilicity, yield, and alpha/beta-selectivity was found. The scaffold contains two orthogonal derivatisation sites, i.e. at O-2' and the anomeric position, and as proof of concept, one derivatised galabioside was synthesized. Compounds based on this galabiose-scaffold are potential inhibitors of P- and P-k-antigen binding proteins. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00475-1
• 作为产物：
  描述：

  1-叠氮-1-脱氧-β-D-吡喃半乳糖苷 在 吡啶 、 盐酸 、 MS AW-300 、 sodium cyanoborohydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醚 、 乙腈 为溶剂， 反应 4.0h， 生成 [(2R,3R,4S,5S,6R)-2-azido-3-benzoyloxy-5-hydroxy-6-(phenylmethoxymethyl)oxan-4-yl] benzoate
  参考文献：
  名称：

  A galabiose-based two-dimensional scaffold for the synthesis of inhibitors targeting Pk- and P-antigen binding proteins

  摘要：

  A disaccharide scaffold based on galabiose (Galal-4Gal) was synthesized. Four different acceptors were evaluated in the alpha-galactosylation and a relationship between the nucleophilicity, yield, and alpha/beta-selectivity was found. The scaffold contains two orthogonal derivatisation sites, i.e. at O-2' and the anomeric position, and as proof of concept, one derivatised galabioside was synthesized. Compounds based on this galabiose-scaffold are potential inhibitors of P- and P-k-antigen binding proteins. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00475-1