methyl O-(4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl)-(1->2)-O-(4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl)-(1->2)-O-(4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl)-(1->2)-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside | 115196-96-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl O-(4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl)-(1->2)-O-(4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl)-(1->2)-O-(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: 115196-96-8
• 化学式: C₅₃H₆₄N₁₂O₁₃
• 分子量: 1077.16
• InChiKey: OYWQBAPCZNSOCO-QXLGJKGDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.19
• 重原子数：
  78.0
• 可旋转键数：
  23.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  326.03
• 氢给体数：
  1.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  methyl O-(4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl)-(1->2)-O-(4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl)-(1->2)-O-(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 palladium on activated charcoal 硫化氢 、 氢气 作用下， 以 吡啶 、 水 、 溶剂黄146 为溶剂， 20.0~40.0 ℃ 、5.0 kPa 条件下， 反应 25.0h， 生成 methyl O-(4,6-dideoxy-4-formamido-α-D-mannopyranosyl)-(1->2)-O-(4,6-dideoxy-4-formamido-α-D-mannopyranosyl)-(1->2)-O-(4,6-dideoxy-4-formamido-α-D-mannopyranosyl)-(1->2)-4,6-dideoxy-4-formamido-α-D-mannopyranoside
  参考文献：
  名称：

  Peters, Thomas; Bundle, David R., Canadian Journal of Chemistry, 1989, vol. 67, p. 491 - 496

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl O-(2-O-acetyl-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl)-(1->2)-O-(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 molecular sieve 、 sodium methylate 、 silver trifluoromethanesulfonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 methyl O-(4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl)-(1->2)-O-(4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl)-(1->2)-O-(4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl)-(1->2)-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside
  参考文献：
  名称：

  Peters, Thomas; Bundle, David R., Canadian Journal of Chemistry, 1989, vol. 67, p. 491 - 496

  摘要：

  DOI：

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。
• [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<br/>[FR] POLYSACCHARIDE ET PROCÉDÉS
  申请人：THE SEC DEP FOR ENVIRONMENT FOOD AND RURAL AFFAIRS

  公开号：WO2018083490A3

  公开（公告）日：2018-08-09
• Synthesis of methyl α-glycosides of some higher oligosaccharide fragments of the O-antigen of Vibrio cholerae O1, serotype Inaba and Ogawa
  作者：Jian Zhang、Pavol Kováč

  DOI：10.1016/s0008-6215(97)00070-0

  日期：1997.5

  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.