2-azido-3,6-di-O-benzyl-2-deoxy-β-D-galactopyranosyl fluoride | 949006-05-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-azido-3,6-di-O-benzyl-2-deoxy-β-D-galactopyranosyl fluoride
• CAS: 949006-05-7
• 化学式: C₂₀H₂₂FN₃O₄
• 分子量: 387.411
• InChiKey: LPYKUWBJMMEVQS-OUUBHVDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.52
• 重原子数：
  28.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  96.68
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-azido-3,6-di-O-benzyl-2-deoxy-β-D-galactopyranosyl fluoride 在 4-二甲氨基吡啶 、 二氯二茂铪 、 4 A molecular sieve 、 silver perchlorate 作用下， 以 吡啶 、 甲苯 为溶剂， 反应 49.0h， 生成 tert-butyldiphenylsilyl 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(3,4,5-trimethoxybenzoyl)-D-galactopyranosyl-(1->3)-2,4-diazido-2,4,6-trideoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of N-linked glycan derived from Gram-negative bacterium, Campylobacter jejuni

  摘要：

  Recent research has revealed the presence of asparagine (Asn)-linked (N-linked) glycoproteins in certain prokaryotes. In this paper, we describe the chemical synthesis of a novel N-glycan derived from Campylobacter jejuni, a heptasaccharide composed of Asn-linked bacillosamine (Bac), repeating GalNAc, and branching Glc, namely GalNAc-alpha(1,4)-GalNAc-alpha(1,4)-[Glc-beta(1,3)-] GalNAc-alpha(1,4)-GalNAc-alpha(1,4)-GalNAc-alpha(1,3)-Bac. The synthesis started from a Bac-acceptor, which was consecutively glycosylated with 4-O-pentafluoropropionyl (PFP) protected donors to give heptasaccharide. Reduction of azide groups was followed by debenzylation to complete the synthesis of the target oligosaccharide. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.126
• 作为产物：
  描述：

  以 吡啶 、 乙醇 为溶剂， 反应 55.5h， 以92%的产率得到2-azido-3,6-di-O-benzyl-2-deoxy-β-D-galactopyranosyl fluoride
  参考文献：
  名称：

  Synthesis of N-linked glycan derived from Gram-negative bacterium, Campylobacter jejuni

  摘要：

  Recent research has revealed the presence of asparagine (Asn)-linked (N-linked) glycoproteins in certain prokaryotes. In this paper, we describe the chemical synthesis of a novel N-glycan derived from Campylobacter jejuni, a heptasaccharide composed of Asn-linked bacillosamine (Bac), repeating GalNAc, and branching Glc, namely GalNAc-alpha(1,4)-GalNAc-alpha(1,4)-[Glc-beta(1,3)-] GalNAc-alpha(1,4)-GalNAc-alpha(1,4)-GalNAc-alpha(1,3)-Bac. The synthesis started from a Bac-acceptor, which was consecutively glycosylated with 4-O-pentafluoropropionyl (PFP) protected donors to give heptasaccharide. Reduction of azide groups was followed by debenzylation to complete the synthesis of the target oligosaccharide. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.126