methyl (2S,4S,5R,6R)-5-acetamido-2-[(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6S)-5-acetamido-4-acetyloxy-2-(acetyloxymethyl)-6-[(2R,3S,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-methoxyoxan-3-yl]oxyoxan-3-yl]oxy-3,5-diacetyloxy-6-(acetyloxymethyl)oxan-4-yl]oxy-4-acetyloxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate | 1053738-04-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (2S,4S,5R,6R)-5-acetamido-2-[(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6S)-5-acetamido-4-acetyloxy-2-(acetyloxymethyl)-6-[(2R,3S,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-methoxyoxan-3-yl]oxyoxan-3-yl]oxy-3,5-diacetyloxy-6-(acetyloxymethyl)oxan-4-yl]oxy-4-acetyloxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 1053738-04-7
• 化学式: C₅₁H₇₄N₂O₃₃
• 分子量: 1243.14
• InChiKey: ITOAPAGNXZZLEQ-LSLSPOLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.9
• 重原子数：
  86
• 可旋转键数：
  35
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  456
• 氢给体数：
  5
• 氢受体数：
  33

反应信息

• 作为反应物：
  描述：

  methyl (2S,4S,5R,6R)-5-acetamido-2-[(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6S)-5-acetamido-4-acetyloxy-2-(acetyloxymethyl)-6-[(2R,3S,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-methoxyoxan-3-yl]oxyoxan-3-yl]oxy-3,5-diacetyloxy-6-(acetyloxymethyl)oxan-4-yl]oxy-4-acetyloxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate 在 sodium hydroxide 、 sodium methylate 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 生成 methyl (5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2-3)-O-(β-D-galactopyranosyl)-(1-4)-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1-2)-α-D-mannopyranoside
  参考文献：
  名称：

  Simplifying Oligosaccharide Synthesis:  Efficient Synthesis of Lactosamine and Siaylated Lactosamine Oligosaccharide Donors

  摘要：

  A practical sequence is described for converting D-glucosamine into peracetylated Gal(beta-1,4)-GlcNTroc(beta1-S)Ph and Neu5Ac(alpha-2,3)Gal(beta-1,4)GlcNTroc(beta1-S)Ph building blocks using a synthetic strategy based on chemoenzymatic oligosaccharide synthesis. The known trichloroethoxycarbonyl, N-Troc, protecting group was selected as a suitable protecting group for both enzymatic and chemical reaction conditions. These oligosaccharide building blocks proved effective donors for the,beta-selective glycosylation of the unreactive OH-3 of a polymeric PEG-bound acceptor and for the axial OH-2 of a mannose acceptor in good yields. The resulting complex oligosaccharides are useful for vaccine and pharmaceutical applications.

  DOI：

  10.1021/jo026569v
• 作为产物：
  描述：

  methyl (2S,4S,5R,6R)-5-acetamido-2-[(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6S)-5-acetamido-4-acetyloxy-2-(acetyloxymethyl)-6-[(2R,3S,4S,5R,6R)-2-methoxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-diacetyloxy-6-(acetyloxymethyl)oxan-4-yl]oxy-4-acetyloxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 16.0h， 生成 methyl (2S,4S,5R,6R)-5-acetamido-2-[(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6S)-5-acetamido-4-acetyloxy-2-(acetyloxymethyl)-6-[(2R,3S,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-methoxyoxan-3-yl]oxyoxan-3-yl]oxy-3,5-diacetyloxy-6-(acetyloxymethyl)oxan-4-yl]oxy-4-acetyloxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
  参考文献：
  名称：

  Simplifying Oligosaccharide Synthesis:  Efficient Synthesis of Lactosamine and Siaylated Lactosamine Oligosaccharide Donors

  摘要：

  A practical sequence is described for converting D-glucosamine into peracetylated Gal(beta-1,4)-GlcNTroc(beta1-S)Ph and Neu5Ac(alpha-2,3)Gal(beta-1,4)GlcNTroc(beta1-S)Ph building blocks using a synthetic strategy based on chemoenzymatic oligosaccharide synthesis. The known trichloroethoxycarbonyl, N-Troc, protecting group was selected as a suitable protecting group for both enzymatic and chemical reaction conditions. These oligosaccharide building blocks proved effective donors for the,beta-selective glycosylation of the unreactive OH-3 of a polymeric PEG-bound acceptor and for the axial OH-2 of a mannose acceptor in good yields. The resulting complex oligosaccharides are useful for vaccine and pharmaceutical applications.

  DOI：

  10.1021/jo026569v