2-aminoethyl 2-acetamido-2-deoxy-α-D-glucopyranosyl-(1->2)-6-O-[(2-(tert-butyloxycarbonylamino)ethyl)phosphono]-L-glycero-α-D-manno-heptopyranosyl-(1->3)-[β-D-glucopyranosyl-(1->4)]-L-glycero-α-D-manno-heptopyranoside | 1169845-91-3

• 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)-6-O-[(2-(tert-butyloxycarbonylamino)ethyl)phosphono]-L-glycero-α-D-manno-heptopyranosyl-(1->3)-[β-D-glucopyranosyl-(1->4)]-L-glycero-α-D-manno-heptopyranoside
• CAS: 1169845-91-3
• 化学式: C₃₇H₆₈N₃O₂₈P
• 分子量: 1033.92
• InChiKey: SXSGVKMPNYVQTL-XMVJUHPISA-N

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-[(benzyl)(2-(tert-butyloxycarbonylamino)ethyl)phosphono]-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 盐酸 、 10% palladium on charcoal 、 水 、 氢气 、 sodium methylate 、 Dowex-H⁽¹⁺⁾ resin 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 24.0h， 以68%的产率得到2-aminoethyl 2-acetamido-2-deoxy-α-D-glucopyranosyl-(1->2)-6-O-[(2-(tert-butyloxycarbonylamino)ethyl)phosphono]-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