phenyl O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2-3)-O-(β-D-galactopyranosyl)-(1-4)-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside | 744193-99-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2-3)-O-(β-D-galactopyranosyl)-(1-4)-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside
• 英文别名: NeuAc(a2-3)Gal(b1-4)[TrocNH(-2d)]Glc(b)-SPh；(2S,4S,5R,6R)-5-acetamido-2-[(2S,3R,4S,5S,6R)-3,5-dihydroxy-2-[(2R,3S,4R,5R,6S)-4-hydroxy-2-(hydroxymethyl)-6-phenylsulfanyl-5-(2,2,2-trichloroethoxycarbonylamino)oxan-3-yl]oxy-6-(hydroxymethyl)oxan-4-yl]oxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• CAS: 744193-99-5
• 化学式: C₃₂H₄₅Cl₃N₂O₁₉S
• 分子量: 900.136
• InChiKey: ZVMHQLHOHJFNOK-SWOFHIPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  57
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  358
• 氢给体数：
  12
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  甲醇 、 phenyl O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2-3)-O-(β-D-galactopyranosyl)-(1-4)-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside 在 Dowex₅₀₀Wx₈-200 resin H⁺ form 作用下， 反应 16.0h， 生成
  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：

  2-氨基-2-脱氧葡萄糖盐酸盐 在 盐酸 、 UDP-galactose 4-epimerase 、 β(1-4)galactosyltransferase 、 sialyltransferase FUS-01/2 、 potassium carbonate 、 magnesium chloride 、 manganese(ll) chloride 作用下， 以 乙醇 、 水 为溶剂， 反应 22.0h， 生成 phenyl O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2-3)-O-(β-D-galactopyranosyl)-(1-4)-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside
  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.