azane;(4R,5R,6R)-6-(1,2-dihydroxyethyl)-2,4,5-trihydroxyoxane-2-carboxylic acid

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: azane;(4R,5R,6R)-6-(1,2-dihydroxyethyl)-2,4,5-trihydroxyoxane-2-carboxylic acid
• 化学式: C₈H₁₄O₈*H₃N
• 分子量: 255.225
• InChiKey: UDJBBKGYARWWNJ-RXHSEFBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.21
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  149
• 氢给体数：
  7
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  azane;(4R,5R,6R)-6-(1,2-dihydroxyethyl)-2,4,5-trihydroxyoxane-2-carboxylic acid 、 乙酸酐 、 溴甲苯 在 吡啶 、 4-二甲氨基吡啶 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 (2,4,5,7,8-penta-O-acetyl-3-deoxy-β-D-manno-oct-2-ulopyranosid)onate
  参考文献：
  名称：

  Synthesis of the Tetrasaccharide Repeating Unit of the β-Kdo-Containing Exopolysaccharide from Burkholderia pseudomallei and B. cepacia Complex

  摘要：

  The synthesis of the repeating unit of the immunogenic beta-Kdo-containing exopolysaccharide produced by Burkholderia pseudomallei and bacteria of the B. cepacia complex is described. The target tetrasaccharide was synthesized via stereoselective 1,2-cis- and 1,2-trans-galactosylations and beta-Kdosylation. A [3 + 1] coupling reaction between a trigalactosyl N-phenyl-2,2,2-trifluoroacetimidate donor and a Kdo acceptor has been successfully achieved for the assembly of the tetrasaccharide skeleton.

  DOI：

  10.1021/acs.joc.5b01823

文献信息

• Synthesis of the Tetrasaccharide Repeating Unit of the β-Kdo-Containing Exopolysaccharide from <i>Burkholderia pseudomallei</i> and <i>B. cepacia</i> Complex
  作者：Anaïs Laroussarie、Barbara Barycza、Hanitra Andriamboavonjy、Marielle Tamigney Kenfack、Yves Blériot、Charles Gauthier

  DOI：10.1021/acs.joc.5b01823

  日期：2015.10.16

  The synthesis of the repeating unit of the immunogenic beta-Kdo-containing exopolysaccharide produced by Burkholderia pseudomallei and bacteria of the B. cepacia complex is described. The target tetrasaccharide was synthesized via stereoselective 1,2-cis- and 1,2-trans-galactosylations and beta-Kdosylation. A [3 + 1] coupling reaction between a trigalactosyl N-phenyl-2,2,2-trifluoroacetimidate donor and a Kdo acceptor has been successfully achieved for the assembly of the tetrasaccharide skeleton.