2,3,4,6,7-penta-O-benzoyl-L-glycero-α-D-manno-heptopyranosyl bromide | 142270-36-8

• 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: 2,3,4,6,7-penta-O-benzoyl-L-glycero-α-D-manno-heptopyranosyl bromide
• CAS: 142270-36-8
• 化学式: C₄₂H₃₃BrO₁₁
• 分子量: 793.621
• InChiKey: OJRHKIDDPYETOF-JVZIWWEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.87
• 重原子数：
  54.0
• 可旋转键数：
  12.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  140.73
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  2,3,4,6,7-penta-O-benzoyl-L-glycero-α-D-manno-heptopyranosyl bromide 、 (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 在 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 0.5h， 以36%的产率得到(2,3,4,6,7-penta-O-benzoyl-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 Branched Heptose- and Kdo-Containing Common Tetrasaccharide Core Structure of Haemophilus influenzae Lipopolysaccharides via a 1,6-Anhydro-l-glycero-β-d-manno-heptopyranose Intermediate

  摘要：

  The synthesis of a common tetrasaccharide core structure of Haemophilus influenzae lipopolysaccharides, beta-D-glucopyranosyl-(1-->4)-[L-glycero-alpha-D-manno-heptopyranosyl-(1-->3)]-L-glycero-alpha-D-manno-heptopyranosyl-(1-->5)-3-deoxy-alpha-D-manno-octulopyranoside and the trisaccharide beta-D-glucopyranosyl-(1-->4)-[L-glycero-alpha-D-manno-heptopyranosyl-(1-->3)]-L-glycero-alpha-D-manno-heptopyranoside is described. The oligosaccharides are synthesized as glycosides of a bifunctional spacer, 2-(4-aminophenyl)ethanol, to allow the subsequent formation of immunogenic glycoconjugates, which will be evaluated as well-defined glycoconjugate vaccine candidates. The syntheses of the 3,4-branched structures were accomplished using a 1,6-anhydro-L-glycero-beta-D-manno-heptopyranose intermediate to diminish the steric crowding between the 3- and 1-substituent. This intermediate was effectively synthesized from a mannose precursor via a stereoselective one-carbon elongation using a Barbier reaction (which was found to be more convenient than a Grignard reaction) and anhydro bridge formation through an internal glycosylation of a 6-O-trimethylsilylated ethyl thioheptoside using NIS/TfOH as a promoter. The 3- and 4-substituent were readily introduced into the 1,6-anhydro intermediate by glycosylation reactions using thioglycosides as donors and NIS/TfOH as a promoter, a task which has not been possible using accepters with equatorial 3,4-substituents. Acetolysis of the anhydro bridge followed by conversion into the ethyl thioglycoside afforded a trisaccharide donor, which, in NIS/TfOH-promoted couplings to the spacer and to a Kdo acceptor followed by deprotection, efficiently gave the two target compounds.

  DOI：

  10.1021/jo9808573

文献信息

• Synthesis of 2-(4-trifluoroacetamidophenyl)ethyl O-(spL-glycero-α-spD-manno-heptopyranosyl)-(1→7)-O-(spL-glycero-α-spD- manno-heptopyranosyl)-(1»3)-spL-glycero-α-spD-manno-heptopyranoside, coresponding to the heptose region of the Salmonella Ra core structure
  作者：Per J. Garegg、Stefan Oscarson、Helena Ritzén、Maria Szönyi

  DOI：10.1016/s0008-6215(00)90553-6

  日期：1992.4

  Abstract The title trisaccharide was synthesized from methyl 2,3,4-tri- O -benzyl- L - glycero -α- D - manno -heptopyranoside by acetolysis, followed by conversion into ethyl thioglycosides and also glycosyl bromides, which were borth used in glycoslyation reactions. In glycosylations using thioglycosides as glycosyl donors, N -iodosuccinimide-silver triflate and dimethyl(methylthio)sulfonium triflate

  摘要标题化合物由2,3,4-三-O-苄基-L-甘油-α-D-甘露聚糖-七吡喃糖苷经乙酰水解合成，然后转化为乙基硫代糖苷和糖基溴化物。糖基化反应。在使用硫代糖苷作为糖基供体的糖基化中，将N-碘代琥珀酰亚胺-三氟甲磺酸银和三氟甲磺酸二甲基（甲硫基）as用作促进剂，并且在与糖基溴化物的糖基化中使用三氟甲磺酸银。设计在标题三糖合成过程中引入中间体的保护基团，以允许在O-3'处进行稍后的糖基化反应，以产生沙门氏菌LPS核心区域的较大寡糖片段，并允许在O-4和0-4'，
• Synthesis of a hexasaccharide corresponding to part of the heptose-hexose region of the Salmonella Ra core, and a penta- and a tetra-saccharide that compose parts of this structure
  作者：Stefan Oscarson、Helena Ritzén

  DOI：10.1016/0008-6215(94)84244-2

  日期：1994.2

  The synthesis of the hexasaccharide 2-(4-trifluoroacetamidophenyl)ethyl O-alpha-D-galactopyranosyl-(1-->3)-[O-alpha-D-galactopyranosyl-(1-->6)]- O-alpha-D-glucopyranosyl-(1-->3)-[O-L-glycero-alpha-D-manno-heptopyranos yl- (1-->7)]-O-L-glycero-alpha-D-manno-heptopyranosyl-(1-->3)-L-glycero-alph a-D- manno-heptopyranoside, corresponding to the heptose and part of the hexose region in the Salmonella Ra

  六糖2-（4-三氟乙酰氨基苯基）乙基O-alpha-D-吡喃半乳糖基-（1-> 3）-[O-alpha-D-吡喃半乳糖基-（1-> 6）]-O-alpha的合成-D-吡喃葡萄糖基-（1-> 3）-[OL-甘油-α-D-甘露聚糖基-（1-> 7）]-OL-甘油-α-D-甘露聚糖基-（1 -> 3）-描述了对应于沙门氏菌Ra核心中的庚糖和部分己糖区域的L-甘油-α-α-D-甘露聚糖-七吡喃糖苷。五糖2-（4-三氟乙酰氨基苯基）乙基O-alpha-D-吡喃半乳糖基-（1-> 3）-O-alpha-D-吡喃葡萄糖基-（1-> 3）-[OL-甘油-α -D-甘露聚糖-七吡喃糖基-（1-> 7）]-OL-甘油-α-D-甘露糖-庚基吡喃糖基-（1-> 3）-L-甘油-α-D-甘露糖基吡喃糖苷和四糖2-（4-三氟乙酰氨基苯基）乙基O-alpha-D-吡喃葡萄糖基-（1-> 3）-[OL-甘油-α-D-甘露庚糖基-（1->