tert-butyldiphenylsilyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside | 904700-88-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyldiphenylsilyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside
• CAS: 904700-88-5
• 化学式: C₄₃H₅₁N₃O₁₄Si
• 分子量: 861.975
• InChiKey: XEGPGCZDHYZFPO-QAWXGAAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.55
• 重原子数：
  61.0
• 可旋转键数：
  13.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  209.34
• 氢给体数：
  0.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  tert-butyldiphenylsilyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside 在 盐酸 、 4 A molecular sieve 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 4.5h， 以90%的产率得到tert-butyldiphenylsilyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->3)-2-azido-6-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：

  tert-butyldiphenylsilyl 2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside 、 甲基2,3,4,6-四-O-乙酰基-1-硫代-β-D-吡喃葡萄糖苷 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 3 A molecular sieve 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 2.0h， 以77%的产率得到tert-butyldiphenylsilyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->3)-2-azido-4,6-O-benzylidene-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