(2S,4S,5R,6R)-5-acetamido-2-[(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6S)-5-(1,3-dioxoisoindol-2-yl)-4-hydroxy-2-(hydroxymethyl)-6-phenylsulfanyloxan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid | 751477-16-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,4S,5R,6R)-5-acetamido-2-[(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6S)-5-(1,3-dioxoisoindol-2-yl)-4-hydroxy-2-(hydroxymethyl)-6-phenylsulfanyloxan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• CAS: 751477-16-4
• 化学式: C₃₇H₄₆N₂O₁₉S
• 分子量: 854.84
• InChiKey: DBNXGEKSIPEYHD-QYIJWXNZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  59
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  357
• 氢给体数：
  11
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (2S,4S,5R,6R)-5-acetamido-2-[(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6S)-5-(1,3-dioxoisoindol-2-yl)-4-hydroxy-2-(hydroxymethyl)-6-phenylsulfanyloxan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid 以 吡啶 为溶剂， 反应 18.0h， 以10 mg的产率得到[(2S,4'S,4aR,5S,5'R,6'R,7R,8S,8aS)-5'-acetamido-4',8-diacetyloxy-5-[(2R,3S,4R,5R,6S)-4-acetyloxy-2-(acetyloxymethyl)-5-(1,3-dioxoisoindol-2-yl)-6-phenylsulfanyloxan-3-yl]oxy-3-oxo-6'-[(1S,2R)-1,2,3-triacetyloxypropyl]spiro[5,7,8,8a-tetrahydro-4aH-pyrano[3,4-b][1,4]dioxine-2,2'-oxane]-7-yl]methyl acetate
  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：

  尿苷(5')二氢二磷酰(1)-alpha-D-葡萄糖 在 UDP-galactose 4-epimerase 、 β(1-4)galactosyltransferase 、 sialyltransferase FUS-01/2 、 magnesium chloride 、 manganese(ll) chloride 作用下， 以 various solvent(s) 为溶剂， 反应 19.0h， 生成 (2S,4S,5R,6R)-5-acetamido-2-[(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6S)-5-(1,3-dioxoisoindol-2-yl)-4-hydroxy-2-(hydroxymethyl)-6-phenylsulfanyloxan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
  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

文献信息

• Simplifying Oligosaccharide Synthesis:  Efficient Synthesis of Lactosamine and Siaylated Lactosamine Oligosaccharide Donors
  作者：Fengyang Yan、Seema Mehta、Eva Eichler、Warren W. Wakarchuk、Michel Gilbert、Melissa J. Schur、Dennis M. Whitfield

  DOI：10.1021/jo026569v

  日期：2003.3.1

  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.