3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-glucopyranosyl-(1->2)-(2'S,3'S)-7-O-benzyl-6-O-chloroacetyl-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-L-glycero-α-D-manno-heptopyranosyl-(1->3)-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->4)]-7-O-acetyl-1,6-anhydro-2-O-benzyl-L-glycero-α-D-manno-heptopyranose | 1169845-81-1

• 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: 3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-glucopyranosyl-(1->2)-(2'S,3'S)-7-O-benzyl-6-O-chloroacetyl-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-L-glycero-α-D-manno-heptopyranosyl-(1->3)-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->4)]-7-O-acetyl-1,6-anhydro-2-O-benzyl-L-glycero-α-D-manno-heptopyranose
• 英文别名: [(2R,3R,4S,5R,6S)-6-[[(1R,2R,3S,4S,5R,7S)-3-[[(2S,3S,4aR,5R,7R,8S,8aS)-5-[(1S)-1-(2-chloroacetyl)oxy-2-phenylmethoxyethyl]-8-[(2S,3R,4R,5S,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-3-azidooxan-2-yl]oxy-2,3-dimethoxy-2,3-dimethyl-5,7,8,8a-tetrahydro-4aH-pyrano[3,4-b][1,4]dioxin-7-yl]oxy]-7-(acetyloxymethyl)-4-phenylmethoxy-6,8-dioxabicyclo[3.2.1]octan-2-yl]oxy]-3,4,5-tribenzoyloxyoxan-2-yl]methyl benzoate
• CAS: 1169845-81-1
• 化学式: C₈₄H₉₀ClN₃O₃₂
• 分子量: 1689.09
• InChiKey: NVTZXIPAEQOGOX-BRJKRLARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  120
• 可旋转键数：
  43
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  380
• 氢给体数：
  0
• 氢受体数：
  34

反应信息

• 作为产物：
  描述：

  (2'S,3'S)-(7-O-benzyl-6-O-chloroacetyl-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-L-glycero-α-D-manno-heptopyranosyl)-(1->3)-[(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(1->4)]-7-O-acetyl-1,6-anhydro-2-O-benzyl-L-glycero-β-D-manno-heptopyranose 、 ethyl 2-azido-2-deoxy-3,4,6-tri-O-acetyl-1-thio-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 silver trifluoromethanesulfonate 作用下， 以 乙醚 为溶剂， 以82%的产率得到3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-glucopyranosyl-(1->2)-(2'S,3'S)-7-O-benzyl-6-O-chloroacetyl-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-L-glycero-α-D-manno-heptopyranosyl-(1->3)-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->4)]-7-O-acetyl-1,6-anhydro-2-O-benzyl-L-glycero-α-D-manno-heptopyranose
  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