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 | 904701-12-8

• 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: 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
• CAS: 904701-12-8
• 化学式: C₅₆H₆₂N₆O₉Si
• 分子量: 991.229
• InChiKey: JUAJINKFBVQQGW-XGOWSAFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.72
• 重原子数：
  72.0
• 可旋转键数：
  22.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  191.59
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  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 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：

  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：

  tert-butyldiphenylsilyl 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-pentafluoropropionyl-α-D-galactopyranosyl-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-galactopyranoside 在 吡啶 作用下， 以 乙醇 为溶剂， 反应 88.0h， 以95%的产率得到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
  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