2-acetamido-1,4,6-tri-O-acetyl-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α,β-D-galactopyranose | 32449-60-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetamido-1,4,6-tri-O-acetyl-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α,β-D-galactopyranose
• 英文别名: [(2R,3R,4R,5R)-5-acetamido-3,6-diacetyloxy-4-[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 32449-60-8；58902-42-4；58902-43-5；62410-05-3；62410-06-4；127444-63-7；127470-01-3
• 化学式: C₂₈H₃₉NO₁₈
• 分子量: 677.614
• InChiKey: HLVYWDMOVAHWGK-UVMRQBHJSA-N

物化性质

• 沸点：
  728.6±60.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.26
• 重原子数：
  47.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  240.89
• 氢给体数：
  1.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  2-acetamido-1,4,6-tri-O-acetyl-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α,β-D-galactopyranose 在 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 D-galactopyranosyl-β-(1,3)-2-acetamido-2-deoxy-α-D-galactopyranose 、 D-galactopyranosyl-β-(1,3)-2-acetamido-2-deoxy-β-D-galactopyranose
  参考文献：
  名称：

  A combined chemical and enzymatic strategy for the construction of carbohydrate-containing antigen core units

  摘要：

  Glycosidase-mediated coupling of glycal acceptors with galactose donors affords beta1,3-linked disaccharides that are versatile intermediates for further chemical and enzymatic manipulation. The utility of these disaccharides is demonstrated by the elaboration of these compounds into the type I and type IV core disaccharides of carbohydrate-containing antigens. Further conversion of the type IV disaccharide to a mucin-type trisaccharide (Galbeta1,3(GlcNAcbeta1,6)GalNAc) was accomplished with the use of a beta1,6-N-acetylglucosaminyltransferase. This combined use of enzymatic and chemical methodologies allows for the rapid assembly, with high regio- and stereoselectivity, of core oligosaccharides of biologically important glycoconjugates.

  DOI：

  10.1021/jo00068a030
• 作为产物：
  描述：

  乙酸酐 、 在 palladium on activated charcoal 氢气 作用下， 反应 14.0h， 生成 2-acetamido-1,4,6-tri-O-acetyl-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α,β-D-galactopyranose
  参考文献：
  名称：

  A combined chemical and enzymatic strategy for the construction of carbohydrate-containing antigen core units

  摘要：

  Glycosidase-mediated coupling of glycal acceptors with galactose donors affords beta1,3-linked disaccharides that are versatile intermediates for further chemical and enzymatic manipulation. The utility of these disaccharides is demonstrated by the elaboration of these compounds into the type I and type IV core disaccharides of carbohydrate-containing antigens. Further conversion of the type IV disaccharide to a mucin-type trisaccharide (Galbeta1,3(GlcNAcbeta1,6)GalNAc) was accomplished with the use of a beta1,6-N-acetylglucosaminyltransferase. This combined use of enzymatic and chemical methodologies allows for the rapid assembly, with high regio- and stereoselectivity, of core oligosaccharides of biologically important glycoconjugates.

  DOI：

  10.1021/jo00068a030

文献信息

• Synthesis of 2-acetamido-2-deoxy-3-O-β-d-galactopyranosyl-d-galactopyranose from 2-acetamido-2-deoxy-d-glucose through a trifluoromethylsulfonyl group displacement
  作者：André Lubineau、Hugues Bienaymé

  DOI：10.1016/0008-6215(91)84064-l

  日期：1991.6
• LUBINEAU, ANDRE;BIENAYME, HUGUES, CARBOHYDR. RES., 212,(1991) C. 267-271
  作者：LUBINEAU, ANDRE、BIENAYME, HUGUES

  DOI：——

  日期：——