phenyl O-(β-D-galactopyranosyl)-(1-4)-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside | 512174-10-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl O-(β-D-galactopyranosyl)-(1-4)-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside
• 英文别名: Gal(b1-4)[TrocNH(-2d)]Glc(b)-SPh；2,2,2-trichloroethyl N-[(2S,3R,4R,5S,6R)-4-hydroxy-6-(hydroxymethyl)-2-phenylsulfanyl-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]carbamate
• CAS: 512174-10-6
• 化学式: C₂₁H₂₈Cl₃NO₁₁S
• 分子量: 608.878
• InChiKey: QBPMOHYIRRZEBM-CPIZOFMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  213
• 氢给体数：
  7
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  phenyl O-(β-D-galactopyranosyl)-(1-4)-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside 在 Dowex₅₀₀Wx₈-200 resin H⁺ form 、 sialyltransferase FUS-01/2 、 magnesium chloride 作用下， 以 various solvent(s) 为溶剂， 反应 18.0h， 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 、 potassium carbonate 、 manganese(ll) chloride 作用下， 以 乙醇 、 水 为溶剂， 反应 20.0h， 生成 phenyl 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.