2-aminoethyl 2-acetamido-2-deoxy-α-D-glucopyranosyl-(1->2)-L-glycero-α-D-manno-heptopyranosyl-(1->3)-[β-D-glucopyranosyl-(1->4)]-L-glycero-α-D-manno-heptopyranoside | 1169845-92-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-aminoethyl 2-acetamido-2-deoxy-α-D-glucopyranosyl-(1->2)-L-glycero-α-D-manno-heptopyranosyl-(1->3)-[β-D-glucopyranosyl-(1->4)]-L-glycero-α-D-manno-heptopyranoside
• 英文别名: GlcNAc(a1-2)LDManHep(a1-3)[Glc(b1-4)]LDManHep(a)-O-EtNH2；N-[(2R,3R,4R,5S,6R)-2-[(2R,3S,4S,5S,6R)-2-[(2S,3S,4R,5R,6R)-2-(2-aminoethoxy)-6-[(1S)-1,2-dihydroxyethyl]-3-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-4-yl]oxy-6-[(1S)-1,2-dihydroxyethyl]-4,5-dihydroxyoxan-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 1169845-92-4
• 化学式: C₃₀H₅₄N₂O₂₃
• 分子量: 810.758
• InChiKey: VSVODSCWJWCAQK-ZTWYXOMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -9.6
• 重原子数：
  55
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  412
• 氢给体数：
  16
• 氢受体数：
  24

反应信息

• 作为产物：
  描述：

  2-(benzyloxycarbonylamino)ethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl-(1->2)-3,4,7-tri-O-acetyl-6-O-chloroacetyl-L-glycero-α-D-manno-heptopyranosyl-(1->3)-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->4)]-6,7-di-O-acetyl-2-O-benzyl-L-glycero-α-D-manno-heptopyranoside 在 sodium methylate 、 盐酸 、 10% palladium on charcoal 、 水 、 氢气 作用下， 以 甲醇 为溶剂， 反应 21.0h， 以92%的产率得到2-aminoethyl 2-acetamido-2-deoxy-α-D-glucopyranosyl-(1->2)-L-glycero-α-D-manno-heptopyranosyl-(1->3)-[β-D-glucopyranosyl-(1->4)]-L-glycero-α-D-manno-heptopyranoside
  参考文献：
  名称：

  Synthesis of phosphorylated Neisseria meningitidis inner core lipopolysaccharide structures

  摘要：

  A phosphoethanolamine-substituted tetrasaccharide structure, 2-aminoethyl 2-acetamido-2-deoxy-alpha-D-glucopyranosyl-(1 -> 2)-6-O-[2-(tert-butyloxycarbonylaminoethyl)-phophono]-L-glycero-alpha-D-manno-heptopyranosyl-(1 -> 3)-[beta-D-glucopyranosyl-(1 -> 4)]-L-glycero-alpha-D-manno-heptopyranoside,corresponding to the non-reducing part of the conserved part of Neisseria meningitidis lipopolysaccharides has been synthesized. Orthogonal protection of the phosphoethanolamino group in combination with the presence of a free amino-containing anomeric spacer allows conjugation to proteins to construct conjugate vaccine candidates. The tetrasaccharide is built up using a linear strategy, where the introduction Of the terminal alpha-GlcNAc moiety is performed using a 2-azido-thioglucoside as a donor and NIS/AgOTf as a promoter. The synthetic pathway includes tetrasaccharide intermediates appropriately designed to permit other phosphorylation patterns as well as elongation at the reducing end. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.02.017