methyl 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl-(1->2)-tetrakis<4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl)-(1->2)>-4-azido-3-O-benzyl-α-D-mannopyranoside | 136737-10-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl-(1->2)-tetrakis<4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl)-(1->2)>-4-azido-3-O-benzyl-α-D-mannopyranoside
• 英文别名: methyl 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl(1→2)4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl(1→2)4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl(1→2)4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl(1→2)4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl(1→2)4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside
• CAS: 136737-10-5
• 化学式: C₇₉H₉₄N₁₈O₁₉
• 分子量: 1599.72
• InChiKey: AAUICTGSOAIQMU-HGISJXFBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.97
• 重原子数：
  116.0
• 可旋转键数：
  35.0
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  478.93
• 氢给体数：
  1.0
• 氢受体数：
  25.0

反应信息

• 作为反应物：
  描述：

  methyl 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl-(1->2)-tetrakis<4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl)-(1->2)>-4-azido-3-O-benzyl-α-D-mannopyranoside 在 硫化氢 作用下， 以 吡啶 、 水 为溶剂， 反应 0.5h， 以91%的产率得到methyl (4-amino-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl)-(1->2)-tetrakis[(4-amino-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl-(1->2)]-4-amino-3-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of methyl α-glycosides of some higher oligosaccharide fragments of the O-antigen of Vibrio cholerae O1, serotype Inaba and Ogawa

  摘要：

  The title oligosaccharides, the tri- through the hexasaccharide in the Inaba series and the penta- and the hexasaccharide in the Ogawa series, have been synthesized using 1-thioglycosides of precursors to 3-O-benzyl-perosamine (4-amino-4,6-dideoxy-D-mannose) as building blocks and N-iodosuccinimide/silver triflate as a promoter. The azido groups in the assembled oligosaccharides were reduced to amino groups, which were then acylated using 2,4-O-benzylidene-3-deoxy-L-glycero-tetronic acid as the derivatizing reagent. Catalytic hydrogenolysis, simultaneously of the benzyl and benzylidene groups, gave the desired products that were characterized by H-1 and C-13 NMR spectroscopy. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00070-0
• 作为产物：
  描述：

  methyl 2-O-acetyl-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl(1→2)4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl(1→2)4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl(1→2)4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl(1→2)4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl(1→2)4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside 在 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 6.0h， 以92.3%的产率得到methyl 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl-(1->2)-tetrakis<4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl)-(1->2)>-4-azido-3-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  [EN] CAPPED OLIGOSACCHARIDES COMPRISING SEVEN OR MORE UNITS OF 4,6-DIDEOXY-4-ACYLAMIDO-ALPHA-PYRANOSE AND CONJUGATES THEREOF AS VACCINES AGAINST INFECTIONS CAUSED BY BRUCELLA ORGANISMS
  [FR] POLYSACCHARIDE ET PROCÉDÉS

  摘要：

  公开号：

  WO2018083490A3

文献信息

• The synthesis of antibody binding-site probes: a hexasaccharide and two pentasaccharides related to the Brucella A antigen and prepared by in situ activation of thioglycosides with bromine
  作者：Jan Kihlberg、David R. Bundle

  DOI：10.1016/0008-6215(92)84151-h

  日期：1992.9

  glycosides. The pentasaccharide analogues each have two formamido groups replaced by hydroxyl groups. Protected derivatives of the three oligosaccharides were prepared by in situ activation with bromine of mono- and di-saccharide thioglycosides of D-rhamnose and 4-azido-4,6-dideoxy-D-mannose in the presence of a glycosyl acceptor and silver triflate as promoter. Reduction of the azido groups with hydrogen sulfide

  制备了两个五糖类似物和布鲁氏菌A抗原[---- 2]-α-D-Rhap4NFo-（1 ----] n的六糖片段作为甲基糖苷，每个五糖类似物具有两个甲酰胺基。三种寡糖的保护衍生物是通过在D-鼠李糖和4-azido-4,6-dideoxy-D-甘露糖存在下用D-鼠李糖和4-azido-4,6-dideoxy-D-甘露糖的单糖和二糖硫糖苷的溴原位活化来制备的。糖基受体和三氟甲磺酸银作为促进剂，用硫化氢还原叠氮基，用甲酸乙酯进行N-甲酰化，然后氢解，得到目标五糖苷。