2-azido-3,6-di-O-benzyl-2-deoxy-4-O-pentafluoropropionyl-β-D-galactopyranosyl fluoride | 904700-86-3

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代烷
• 英文名称: 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-pentafluoropropionyl-β-D-galactopyranosyl fluoride
• 英文别名: [(2R,3R,4R,5R,6S)-5-azido-6-fluoro-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl] 2,2,3,3,3-pentafluoropropanoate
• CAS: 904700-86-3
• 化学式: C₂₃H₂₁F₆N₃O₅
• 分子量: 533.427
• InChiKey: GQTWLHMXXAKIRM-OUUBHVDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  68.4
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  2-azido-3,6-di-O-benzyl-2-deoxy-4-O-pentafluoropropionyl-β-D-galactopyranosyl fluoride 、 tert-butyldiphenylsilyl 2-azido-3,6-di-O-benzyl-2-deoxy-α-D-galactopyranosyl-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-galactopyranoside 在 二氯二茂铪 、 4 A molecular sieve 、 silver perchlorate 作用下， 以 氯仿 为溶剂， 反应 42.0h， 以80%的产率得到tert-butyldiphenylsilyl 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-pentafluoropropionyl-D-galactopyranosyl-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-galactopyranosyl-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-galactopyranoside
  参考文献：
  名称：

  A stereoselective 1,2-cis glycosylation toward the synthesis of a novel N-linked glycan from the Gram-negative bacterium, Campylobacter jejuni

  摘要：

  It has been shown that certain prokaryotes, such as Campylobacter jejuni, have asparagine (Asn)-linked glycoproteins. However, the structures of their glycans are distinct from those of eukaryotic origin. They consist of a bacillosamine residue linked to Asn, an alpha-(1 -> 4)-GalpNAc repeat, and a branching beta-Glcp residue. In this paper, we describe a strategy for the stereoselective construction of the alpha-(1 -> 4)-GalpNAc repeat of a C. jejuni N-glycan, utilizing a pentafluoropropionyl (PFP) group as a temporary protective group of the C-4 OH group of the GalpN donor. The strategy was applied to the synthesis of the hexasaccharide alpha-Galp-NAc-(1 -> 4)-alpha-GalpNAc-(1 -> 4)-[beta-Glcp-(1 -> 3)]-alpha-GalpNAc(1 -> 4)-alpha-GalpNAc-(1 -> 4)-GalpNAc. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.03.011
• 作为产物：
  描述：

  2-azido-3,6-di-O-benzyl-2-deoxy-4-O-pentafluoropropionyl-D-galactopyranose 在 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-pentafluoropropionyl-β-D-galactopyranosyl fluoride 、 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-pentafluoropropionyl-α-D-galactopyranosyl fluoride
  参考文献：
  名称：

  A stereoselective 1,2-cis glycosylation toward the synthesis of a novel N-linked glycan from the Gram-negative bacterium, Campylobacter jejuni

  摘要：

  It has been shown that certain prokaryotes, such as Campylobacter jejuni, have asparagine (Asn)-linked glycoproteins. However, the structures of their glycans are distinct from those of eukaryotic origin. They consist of a bacillosamine residue linked to Asn, an alpha-(1 -> 4)-GalpNAc repeat, and a branching beta-Glcp residue. In this paper, we describe a strategy for the stereoselective construction of the alpha-(1 -> 4)-GalpNAc repeat of a C. jejuni N-glycan, utilizing a pentafluoropropionyl (PFP) group as a temporary protective group of the C-4 OH group of the GalpN donor. The strategy was applied to the synthesis of the hexasaccharide alpha-Galp-NAc-(1 -> 4)-alpha-GalpNAc-(1 -> 4)-[beta-Glcp-(1 -> 3)]-alpha-GalpNAc(1 -> 4)-alpha-GalpNAc-(1 -> 4)-GalpNAc. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.03.011