ethyl 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)-1-thio-L-glycero-α-D-manno-heptopyranoside S-oxide | 1169845-78-6

• 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: ethyl 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)-1-thio-L-glycero-α-D-manno-heptopyranoside S-oxide
• CAS: 1169845-78-6
• 化学式: C₃₆H₅₀ClN₃O₁₇S
• 分子量: 864.322
• InChiKey: YTTNSLWYSGUHOV-JBDNZGNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.57
• 重原子数：
  58.0
• 可旋转键数：
  18.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  244.87
• 氢给体数：
  0.0
• 氢受体数：
  18.0

反应信息

• 作为产物：
  描述：

  ethyl 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)-1-thio-L-glycero-α-D-manno-heptopyranoside 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以61%的产率得到ethyl 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)-1-thio-L-glycero-α-D-manno-heptopyranoside S-oxide
  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