(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 | 1023637-07-1

• 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: (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
• 英文别名: (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；[(2R,3R,4S,5R,6S)-6-[[(1R,2R,3S,4S,5R,7S)-3-[[(2S,3S,4aR,5R,7R,8S,8aR)-5-[(1S)-1-(2-chloroacetyl)oxy-2-phenylmethoxyethyl]-8-hydroxy-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: 1023637-07-1
• 化学式: C₇₂H₇₅ClO₂₅
• 分子量: 1375.83
• InChiKey: VJQPVYWNCMMOGZ-HONMOIOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  98
• 可旋转键数：
  33
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  289
• 氢给体数：
  1
• 氢受体数：
  25

反应信息

• 作为反应物：
  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 2,3,4,6,7-penta-O-benzoyl-1-thio-L-glycero-α-D-manno-heptopyranoside 在 N-碘代丁二酰亚胺 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以86%的产率得到(2'S,3'S)-(2,3,4,6,7-penta-O-benzoyl-L-glycero-α-D-manno-heptopyranosyl)-(1->2)-(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
  参考文献：
  名称：

  Synthesis of a common tetrasaccharide motif of Haemophilus influenzae LPS inner core structures

  摘要：

  一种保守的四糖结构，L-glycero-α-D-manno-heptopyranosyl-(1→2)-(6-O-氨乙基膦酸-L-glycero-α-D-manno-heptopyranosyl)-(1→3)-[β-D-glucopyranosyl-(1→4)]-L-glycero-α-D-manno-heptopyranose，已从流感嗜血杆菌的LPS内核中合成为其乙基氨基糖苷，以便于后续的连接。从先前合成的适当保护的三糖中间体开始，引入了第三个七碳糖，随后通过硫糖苷供体化学引入了连接体。磷酸乙醇胺是通过使用Boc保护的磷酸酰胺化合物形成的。最后去保护并与生物素连接，得到的结合物将用于研究针对天然LPS结构的单克隆抗体的特异性。

  DOI：

  10.1039/b717564g
• 作为产物：
  描述：

  在 水 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以76%的产率得到(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
  参考文献：
  名称：

  Synthesis of a common tetrasaccharide motif of Haemophilus influenzae LPS inner core structures

  摘要：

  一种保守的四糖结构，L-glycero-α-D-manno-heptopyranosyl-(1→2)-(6-O-氨乙基膦酸-L-glycero-α-D-manno-heptopyranosyl)-(1→3)-[β-D-glucopyranosyl-(1→4)]-L-glycero-α-D-manno-heptopyranose，已从流感嗜血杆菌的LPS内核中合成为其乙基氨基糖苷，以便于后续的连接。从先前合成的适当保护的三糖中间体开始，引入了第三个七碳糖，随后通过硫糖苷供体化学引入了连接体。磷酸乙醇胺是通过使用Boc保护的磷酸酰胺化合物形成的。最后去保护并与生物素连接，得到的结合物将用于研究针对天然LPS结构的单克隆抗体的特异性。

  DOI：

  10.1039/b717564g

文献信息

• Synthesis of phosphorylated Neisseria meningitidis inner core lipopolysaccharide structures
  作者：Johan D.M. Olsson、Stefan Oscarson

  DOI：10.1016/j.tetasy.2009.02.017

  日期：2009.5

  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.
• Synthesis of a common tetrasaccharide motif of Haemophilus influenzae LPS inner core structures
  作者：Karin Mannerstedt、Eva Segerstedt、Johan Olsson、Stefan Oscarson

  DOI：10.1039/b717564g

  日期：——

  A conserved tetrasaccharide structure, L-glycero-α-D-manno-heptopyranosyl-(1→2)-(6-O-aminoethylphosphono-L-glycero-α-D-manno-heptopyranosyl)-(1→3)-[β-D-glucopyranosyl-(1→4)]-L-glycero-α-D-manno-heptopyranose, from the LPS inner core of Haemophilus influenzae has been synthesised as its ethylamino glycosides to allow later conjugations. Starting from a previously synthesised suitably protected trisaccharide intermediate, the third heptose and subsequently the spacer were introduced using thioglycoside donor chemistry. The phosphoethanolamine was formed employing a Boc-protected phosphoamidite. Final deprotection and conjugation to biotin gave conjugates that will be used to study the specificity of MAbs raised against native LPS structures.

  一种保守的四糖结构，L-glycero-α-D-manno-heptopyranosyl-(1→2)-(6-O-氨乙基膦酸-L-glycero-α-D-manno-heptopyranosyl)-(1→3)-[β-D-glucopyranosyl-(1→4)]-L-glycero-α-D-manno-heptopyranose，已从流感嗜血杆菌的LPS内核中合成为其乙基氨基糖苷，以便于后续的连接。从先前合成的适当保护的三糖中间体开始，引入了第三个七碳糖，随后通过硫糖苷供体化学引入了连接体。磷酸乙醇胺是通过使用Boc保护的磷酸酰胺化合物形成的。最后去保护并与生物素连接，得到的结合物将用于研究针对天然LPS结构的单克隆抗体的特异性。