6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-mannopyranosyl trichloroacetimidate | 154970-29-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-mannopyranosyl trichloroacetimidate
• CAS: 154970-29-3
• 化学式: C₂₄H₂₅Cl₃N₄O₆
• 分子量: 571.845
• InChiKey: ZLPSPCBQPLCOIH-PVIWCNJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.49
• 重原子数：
  37.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  135.83
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-mannopyranosyl trichloroacetimidate 在 N-碘代丁二酰亚胺 、 (1,5-cyclooctadiene)bis(methyldiphenylphosphine) iridium hexafluorophosphate 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 potassium tert-butylate 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 methyl 2,4-di-O-benzyl-3-O-(2-azido-3,4-di-O-benzyl-2-deoxy-α-D-mannopyranosyl)-6-O-(2-azido-3,4-di-O-benzyl-2-deoxy-α-D-mannopyranosyl)-α-D-mannopyranoside
  参考文献：
  名称：

  Spijker, Nynke M.; Slief, Jan-Willem; Boeckel, Constant A. A. van, Journal of Carbohydrate Chemistry, 1993, vol. 12, # 8, p. 1017 - 1042

  摘要：

  DOI：
• 作为产物：
  描述：

  1,6-di-O-acetyl-2-azido-2-deoxy-3,4-di-O-benzyl-D-glucopyranose 在 哌啶 、 potassium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-mannopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Spijker, Nynke M.; Slief, Jan-Willem; Boeckel, Constant A. A. van, Journal of Carbohydrate Chemistry, 1993, vol. 12, # 8, p. 1017 - 1042

  摘要：

  DOI：

文献信息

• Towards a Synthetic Glycoconjugate Vaccine Against Neisseria meningitidis A
  作者：Ali Berkin、Bruce Coxon、Vince Pozsgay

  DOI：10.1002/1521-3765(20021004)8:19<4424::aid-chem4424>3.0.co;2-1

  日期：2002.10.4

  Albumin conjugates of synthetic fragments of the capsular polysaccharide of the Gram-negative bacterium Neisseria meningitidis serogroup A were prepared. The fragments include monosaccharides 1 [alpha-D-ManpNAc(1--> 0)-(CH2)(2)NH2] and 2 [6-O-P(O)-(O-)(2)-alpha-D-ManpNAc-(1 --> O)-(CH2)(2)NH2] ,disaccharide 3 [alpha-D-ManpNAc[1-->O-P(O)(O-) --> 6]-alpha-D-ManpNAc(1 --> O)-(CH2)(2)NH2], and trisaccharide 4 [alpha-D-ManpNAc-[1 -->O-P(O)(O-)--> 6]-alpha-D-ManpNAc-[1 -->O-P(O)(O-)--> 6]-alpha-D-ManpNAc-(1 --> O)-(CH2)(2)NH2]. Two monosaccharide blocks were employed as key intermediates. The reduc-ing-end mannose unit featured the NHAc group at C-2, and contained the aminoethyl spacer as the aglycon for the final bioconjugation. The interresidual phosphodiester linkages were fashioned from an anomerically positioned H-phosphonate group in a 2-azido-man-nose building block. The spacer-linked saccharides 1-4 were N-acylated with hepta-4,6-dienoic acid and the resulting conjugated diene-equipped saccharides were subjected to Diels-Alder-type addition with maleimidobutyryl-group functionalized human serum albumin to form covalent conjugates containing up to 26 saccharide haptens per albumin molecule. Complete H-1, C-13, and P-31 NMR assignments for 1-4 are given. Antigenicity of the neoglycoconjugates containing 1-4 was demonstrated by a double immunodiffusion assay which indicated that a fragment as small as a monosaccharide is recognized by a polyclonal meningococcus group A antiserum and that the O-acetyl group(s) present in the natural capsular material is not essential for antigenicity.
• Van Den Broek; Kat-Van Den Nieuwenhof; Butters, Journal of Pharmacy and Pharmacology, 1996, vol. 48, # 2, p. 172 - 178
  作者：Van Den Broek、Kat-Van Den Nieuwenhof、Butters、Van Boeckel

  DOI：——

  日期：——