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-α-D-mannopyranoside | 115196-86-6

• 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)-(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 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；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-mannopyranoside；(2R,3S,4S,5R,6R)-5-azido-2-[(2R,3S,4S,5R,6R)-5-azido-2-[(2S,3S,4S,5R,6R)-5-azido-2-methoxy-6-methyl-4-phenylmethoxyoxan-3-yl]oxy-6-methyl-4-phenylmethoxyoxan-3-yl]oxy-6-methyl-4-phenylmethoxyoxan-3-ol
• CAS: 115196-86-6
• 化学式: C₄₀H₄₉N₉O₁₀
• 分子量: 815.883
• InChiKey: YHSHJIYQURSDPA-SBJYFIKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.79
• 重原子数：
  59.0
• 可旋转键数：
  17.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  249.58
• 氢给体数：
  1.0
• 氢受体数：
  13.0

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)-(4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl-(1->2)-4-azido-3-O-benzyl-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)-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 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 6.0h， 以91.2%的产率得到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-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

• Synthesis of 4,6-dideoxy-4-formamido-α-<scp>D</scp>-mannose containing tri-, tetra-, and penta-saccharides, antigenic determinants of the Brucella A and M antigens
  作者：Thomas Peters、David R. Bundle

  DOI：10.1039/c39870001648

  日期：——

  synthetic strategy based upon the use of thioglycosides to generate 1,2-trans-glycosidic linkages has been developed and has permitted efficient synthesis of pentameric α-1,2 linked 4,6-dideoxy-4-formamido-α-D-mannose homo-oligomers as well as structures containing α-1,3 linkages.

  已经开发了基于使用硫代糖苷生成1,2-反式-糖苷键的合成策略，该策略已使五聚体α-1,2连接的4,6-二脱氧-4-甲酰胺基-α - D-甘露糖有效合成。均聚物以及包含α-1,3键的结构。
• Peters, Thomas; Bundle, David R., Canadian Journal of Chemistry, 1989, vol. 67, p. 497 - 502
  作者：Peters, Thomas、Bundle, David R.

  DOI：——

  日期：——
• 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.
• PETERS, THOMAS;BUNDLE, DAVID R., CAN. J. CHEM., 67,(1989) N, C. 491-496
  作者：PETERS, THOMAS、BUNDLE, DAVID R.

  DOI：——

  日期：——