3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl-(1->2)-7-O-benzyl-6-O-chloroacetyl-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 | 1169845-82-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl-(1->2)-7-O-benzyl-6-O-chloroacetyl-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
• CAS: 1169845-82-2
• 化学式: C₇₈H₈₀ClN₃O₃₀
• 分子量: 1574.95
• InChiKey: KPQWBPMYVPHHLP-JAYBPKOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.32
• 重原子数：
  112.0
• 可旋转键数：
  32.0
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  418.22
• 氢给体数：
  2.0
• 氢受体数：
  31.0

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl-(1->2)-7-O-benzyl-6-O-chloroacetyl-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 、 乙酸酐 在 scandium tris(trifluoromethanesulfonate) 作用下， 反应 2.0h， 以96%的产率得到3,4,6-tri-O-acetyl-2-azido-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)]-1,6,7-tri-O-acetyl-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
• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-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 在 水 、 三氟乙酸 作用下， 反应 0.33h， 以86%的产率得到3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl-(1->2)-7-O-benzyl-6-O-chloroacetyl-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