[(2S,3R,4R,5R,6R)-3-azido-5-(naphthalen-2-ylmethoxy)-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-2-yl]oxy-tert-butyl-diphenylsilane | 949006-01-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: [(2S,3R,4R,5R,6R)-3-azido-5-(naphthalen-2-ylmethoxy)-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-2-yl]oxy-tert-butyl-diphenylsilane
• CAS: 949006-01-3
• 化学式: C₄₇H₄₉N₃O₅Si
• 分子量: 764.009
• InChiKey: INMMYCVTKBODEI-PSKPMRIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.51
• 重原子数：
  56
• 可旋转键数：
  16
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  60.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(2S,3R,4R,5R,6R)-3-azido-5-(naphthalen-2-ylmethoxy)-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-2-yl]oxy-tert-butyl-diphenylsilane 在 二乙胺基三氟化硫 、 氟化氢吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 16.0h， 生成
  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-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside 在 盐酸 、 四丁基碘化铵 、 sodium hydride 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 为溶剂， 反应 9.0h， 生成 [(2S,3R,4R,5R,6R)-3-azido-5-(naphthalen-2-ylmethoxy)-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-2-yl]oxy-tert-butyl-diphenylsilane
  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

文献信息

• Synthesis of N-linked glycan derived from Gram-negative bacterium, Campylobacter jejuni
  作者：Mohammed Nurul Amin、Akihiro Ishiwata、Yukishige Ito

  DOI：10.1016/j.tet.2007.05.126

  日期：2007.8

  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.