2-(benzyloxycarbonylamino)ethyl 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-mannopyranoside | 497096-18-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-(benzyloxycarbonylamino)ethyl 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-mannopyranoside
• CAS: 497096-18-1
• 化学式: C₃₂H₃₆N₄O₈
• 分子量: 604.66
• InChiKey: UKZUKVIELQZLSO-DUWVOHMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.07
• 重原子数：
  44.0
• 可旋转键数：
  15.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  150.31
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2-(benzyloxycarbonylamino)ethyl 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-mannopyranoside 在 sodium tetrahydroborate 、 nickel dichloride 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 Acetic acid (2R,3S,4R,5S,6S)-5-amino-3,4-bis-benzyloxy-6-(2-benzyloxycarbonylamino-ethoxy)-tetrahydro-pyran-2-ylmethyl ester
  参考文献：
  名称：

  Towards a Synthetic Glycoconjugate Vaccine Against Neisseria meningitidis A

  摘要：

  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.

  DOI：

  10.1002/1521-3765(20021004)8:19<4424::aid-chem4424>3.0.co;2-1
• 作为产物：
  描述：

  6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-mannopyranose 在 三氟甲磺酸三甲基硅酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 2-(benzyloxycarbonylamino)ethyl 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-mannopyranoside
  参考文献：
  名称：

  Towards a Synthetic Glycoconjugate Vaccine Against Neisseria meningitidis A

  摘要：

  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.

  DOI：

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