5-acetamido-2,6-anhydro-3,5-dideoxy-8-O-(5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosyl)-D-glycero-D-galacto-non-2-enopyranose | 115014-04-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-acetamido-2,6-anhydro-3,5-dideoxy-8-O-(5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosyl)-D-glycero-D-galacto-non-2-enopyranose
• 英文别名: (2R,3R,4S)-3-acetamido-2-[(1S,2R)-2-[(2S,4S,5R,6R)-5-acetamido-2-carboxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxy-1,3-dihydroxypropyl]-4-hydroxy-3,4-dihydro-2H-pyran-6-carboxylic acid
• CAS: 115014-04-5
• 化学式: C₂₂H₃₄N₂O₁₆
• 分子量: 582.516
• InChiKey: LAACAIZCSQPIAB-VJMNTEOVSA-N

物化性质

• 沸点：
  1132.6±65.0 °C(predicted)
• 密度：
  1.67±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -5.89
• 重原子数：
  40.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  302.1
• 氢给体数：
  11.0
• 氢受体数：
  14.0

反应信息

• 作为产物：
  描述：

  (4S,5R,6R)-5-Acetylamino-6-{(1S,2R)-2-[(2S,4S,5R,6R)-5-acetylamino-4-hydroxy-2-methoxycarbonyl-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-yloxy]-1,3-dihydroxy-propyl}-4-hydroxy-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 5-acetamido-2,6-anhydro-3,5-dideoxy-8-O-(5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosyl)-D-glycero-D-galacto-non-2-enopyranose
  参考文献：
  名称：

  Syntheses of (α2–9) and (α2–8) linked neuraminylneuraminic acid derivatives

  摘要：

  DOI：

  10.1016/s0040-4039(00)85176-x

文献信息

• Syntheses of (α2–9) and (α2–8) linked dineuraminyl saccharides by use of 2β-bromo-3β-hydroxy-4,7,8,9-tetra--acetyl--acetylneuraminic acid methyl ester1
  作者：Kaoru Okamoto、Tadao Kondo、Toshio Goto

  DOI：10.1016/s0040-4020(01)85909-3

  日期：1988.1

  disacchrides, which are involved in the group C meningococcal polysaccharides and gangliosides, were synthesized by condensation of the acetyl protected 2-deoxy-2,3-dehydroneuraminic acid methyl ester having a hydroxyl group at 9 or 8 position with the acetyl protected 2β-bromo-3β-hydroxy-N-acetylneuraminic ester in preference to the corresponding β-glycosides. The hydroxyl groups of the obtained glycosides were

  NeuAc（α2–9）NeuAc和NeuAc（α2–8）NeuAc二元化合物与C组脑膜炎球菌多糖和神经节苷脂有关，是通过乙酰保护的2-脱氧-2,3-脱氢尿嘧啶酸甲酯的缩合反应合成的。与相应的β-糖苷相比，乙酰保护的2β-溴-3β-羟基-N-乙酰神经氨酸酯在9或8位具有一个羟基。通过苯氧硫羰基化除去所得糖苷的羟基，然后用三丁基锡烷还原，并将所得的二糖脱保护，以高收率得到游离糖苷。
• OKAMOTO, KAORU;KONDO, TADAO;GOTO, TOSCIO, TETRAHEDRON, 43,(1987) N 24, 5909-5918
  作者：OKAMOTO, KAORU、KONDO, TADAO、GOTO, TOSCIO

  DOI：——

  日期：——