β-D-galactofuranosyl-(1->3)-D-galactopyranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-D-galactofuranosyl-(1->3)-D-galactopyranose
• 英文别名: Galf(b1-3)Galf；(2S,3R,4R,5S)-2-[(1R)-1,2-dihydroxyethyl]-5-[(2S,3R,4R)-2-[(1R)-1,2-dihydroxyethyl]-4,5-dihydroxyoxolan-3-yl]oxyoxolane-3,4-diol
• 化学式: C₁₂H₂₂O₁₁
• 分子量: 342.3
• InChiKey: JNOVOCXIHZGVIV-OLRYEBKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.7
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  190
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  D-吡喃葡萄糖 在 三氟甲磺酸三甲基硅酯 吡啶 、 Dowex 50 (H⁺) 、 MS 4 Angstroem 、 氨 、 溶剂黄146 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 131.0h， 生成 β-D-galactofuranosyl-(1->3)-D-galactopyranose
  参考文献：
  名称：

  First synthesis of β-d-Galf-(1→3)-d-Galp—the repeating unit of the backbone structure of the O-antigenic polysaccharide present in the lipopolysaccharide (LPS) of the genus Klebsiella

  摘要：

  b-D-Galactofuranosyl-(1 --> 3)-D-galactopyranose (1), the repeating unit of the backbone structure of the O-antigenic polysaccharide present in the lipopolysaccharide (LPS) of the genus Klebsiella, has been efficiently synthesized using 1,2:5,6-di-O-isopropylidine-alpha-D-galactofuranose (3) as the glycosyl acceptor and 2,3,5,6-tetra-0-benzoyl-p-D-galactofuranosyl trichloroacetimidate (6) as the glycosyl donor with TMSOTf as catalyst by the well-known Schmidt glycosylation method. The preparation of 3 was improved by increasing the ratio of DMF to acetone and employing a solid-supported catalyst. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00076-4

文献信息

• First synthesis of β-d-Galf-(1→3)-d-Galp—the repeating unit of the backbone structure of the O-antigenic polysaccharide present in the lipopolysaccharide (LPS) of the genus Klebsiella
  作者：Hairong Wang、Guohua Zhang、Jun Ning

  DOI：10.1016/s0008-6215(03)00076-4

  日期：2003.5

  b-D-Galactofuranosyl-(1 --> 3)-D-galactopyranose (1), the repeating unit of the backbone structure of the O-antigenic polysaccharide present in the lipopolysaccharide (LPS) of the genus Klebsiella, has been efficiently synthesized using 1,2:5,6-di-O-isopropylidine-alpha-D-galactofuranose (3) as the glycosyl acceptor and 2,3,5,6-tetra-0-benzoyl-p-D-galactofuranosyl trichloroacetimidate (6) as the glycosyl donor with TMSOTf as catalyst by the well-known Schmidt glycosylation method. The preparation of 3 was improved by increasing the ratio of DMF to acetone and employing a solid-supported catalyst. (C) 2003 Elsevier Science Ltd. All rights reserved.