2-aminoethyl (2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1→3)-(α-D-galactopyranosyl)-(1→3)-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1→2)-(α-D-glucopyranosyl)-(1→6)-α-D-glucopyranoside | 1554556-38-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-aminoethyl (2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1→3)-(α-D-galactopyranosyl)-(1→3)-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1→2)-(α-D-glucopyranosyl)-(1→6)-α-D-glucopyranoside
• 英文别名: GlcNAc(b1-3)Gal(a1-3)GlcNAc(b1-2)Glc(a1-6)Glc(a)-O-EtNH2；N-[(2S,3R,4R,5S,6R)-2-[(2S,3R,4S,5S,6R)-2-[(2S,3R,4R,5S,6R)-3-acetamido-2-[(2S,3R,4S,5S,6R)-2-[[(2R,3S,4S,5R,6S)-6-(2-aminoethoxy)-3,4,5-trihydroxyoxan-2-yl]methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 1554556-38-5
• 化学式: C₃₆H₆₃N₃O₂₆
• 分子量: 953.901
• InChiKey: ZURHVZHMSQQDKA-OWFYAHEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -9.9
• 重原子数：
  65
• 可旋转键数：
  18
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  460
• 氢给体数：
  17
• 氢受体数：
  27

反应信息

• 作为产物：
  描述：

  在 三乙基硅烷 、 20% palladium hydroxide-activated charcoal 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 10.5h， 以185 mg的产率得到2-aminoethyl (2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1→3)-(α-D-galactopyranosyl)-(1→3)-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1→2)-(α-D-glucopyranosyl)-(1→6)-α-D-glucopyranoside
  参考文献：
  名称：

  Convergent synthesis of a pentasaccharide repeating unit corresponding to the cell wall O-antigen of Salmonella enterica O44

  摘要：

  A convergent synthetic strategy has been developed for the synthesis of a pentasaccharide fragment corresponding to the O-antigen of Salmonella enterica 044 strain. An intermediate tetrasaccharide derivative was prepared by a [2+2] block glycosylation of two disaccharide derivatives. The p-methoxybenzyl (PMB) group has been used as the in situ temporary protecting group minimizing the number of functional group manipulation steps. The application of the armed-disarmed glycosylation concept reduced the number of steps in the synthetic strategy. The glycosylation steps were highly stereoselective and high yielding. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.12.005