pivaloyl(-3)[pivaloyl(-6)]Gal2Ac4Ac(b1-4)[pivaloyl(-6)]GlcNAc(b)-O-Bn | 212198-13-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: pivaloyl(-3)[pivaloyl(-6)]Gal2Ac4Ac(b1-4)[pivaloyl(-6)]GlcNAc(b)-O-Bn
• 英文别名: [(2R,3S,4R,5R,6R)-5-acetamido-3-[(2S,3R,4S,5S,6R)-3,5-diacetyloxy-4-(2,2-dimethylpropanoyloxy)-6-(2,2-dimethylpropanoyloxymethyl)oxan-2-yl]oxy-4-hydroxy-6-phenylmethoxyoxan-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 212198-13-5
• 化学式: C₄₀H₅₉NO₁₆
• 分子量: 809.906
• InChiKey: QAPJZDIDWWJHKX-HQHFHPRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  57
• 可旋转键数：
  21
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  218
• 氢给体数：
  2
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  pivaloyl(-3)[pivaloyl(-6)]Gal2Ac4Ac(b1-4)[pivaloyl(-6)]GlcNAc(b)-O-Bn 、 [(2R,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl] N-phenylcarbamate 在 三氟甲磺酸三甲基硅酯 、 4 Angstroem MS 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以58%的产率得到benzyl O-(2,4-di-O-acetyl-3,6-di-O-pivaloyl-β-D-galactopyranosyl)-(1->4)-O-[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)]-2-acetamido-2-deoxy-6-O-pivaloyl-β-D-glucopyranoside
  参考文献：
  名称：

  Novel Synthetic Approaches to Manβ1-4GLCNAc and Lex Units from N-Acetyllactosamine

  摘要：

  Regioselective protection of N-acetyllactosamine with triphenylmethyl (trityl) and pivaloyl groups afforded the corresponding 3, 2', 4'-tri- and 2',4'-dihydroxyl derivatives in a few steps, respectively; these derivatives were used efficiently for the syntheses of the title compounds from N-acetyllactosamine in 46% (7 steps) and 19% (8 steps) overall yields, respectively.

  DOI：

  10.1080/07328309808002347
• 作为产物：
  描述：

  [(2R,3S,4S,5R,6S)-6-[(2R,3S,4R,5R,6R)-5-acetamido-2-(2,2-dimethylpropanoyloxymethyl)-6-phenylmethoxy-4-(2,2,2-trichloroethoxycarbonyloxy)oxan-3-yl]oxy-4-(2,2-dimethylpropanoyloxy)-3,5-dihydroxyoxan-2-yl]methyl 2,2-dimethylpropanoate 在 水 、 锌 作用下， 以 吡啶 、 溶剂黄146 为溶剂， 反应 1.0h， 生成 pivaloyl(-3)[pivaloyl(-6)]Gal2Ac4Ac(b1-4)[pivaloyl(-6)]GlcNAc(b)-O-Bn
  参考文献：
  名称：

  Novel Synthetic Approaches to Manβ1-4GLCNAc and Lex Units from N-Acetyllactosamine

  摘要：

  Regioselective protection of N-acetyllactosamine with triphenylmethyl (trityl) and pivaloyl groups afforded the corresponding 3, 2', 4'-tri- and 2',4'-dihydroxyl derivatives in a few steps, respectively; these derivatives were used efficiently for the syntheses of the title compounds from N-acetyllactosamine in 46% (7 steps) and 19% (8 steps) overall yields, respectively.

  DOI：

  10.1080/07328309808002347