methyl 6-azido-[2,3-b](11,12-benzo-1,4,7,10,13,16-hexaoxacyclooctadeca-11-ene)-4-O-(2-hydroxy-ethane-1-yl)-2,3,6-trideoxy-α-D-glucopyranoside | 260414-03-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-azido-[2,3-b](11,12-benzo-1,4,7,10,13,16-hexaoxacyclooctadeca-11-ene)-4-O-(2-hydroxy-ethane-1-yl)-2,3,6-trideoxy-α-D-glucopyranoside
• 英文别名: 2-[[(9R,10S,12R,13R,14S)-12-(azidomethyl)-10-methoxy-2,5,8,11,15,18,21-heptaoxatricyclo[20.4.0.09,14]hexacosa-1(26),22,24-trien-13-yl]oxy]ethanol
• CAS: 260414-03-7
• 化学式: C₂₃H₃₅N₃O₁₀
• 分子量: 513.545
• InChiKey: VDARQWTWYMIZIK-ZQGJOIPISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-acetyl-D-galactopyranosyl trichloroacetimidate 、 methyl 6-azido-[2,3-b](11,12-benzo-1,4,7,10,13,16-hexaoxacyclooctadeca-11-ene)-4-O-(2-hydroxy-ethane-1-yl)-2,3,6-trideoxy-α-D-glucopyranoside 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以57%的产率得到methyl 6-azido-[2,3-b](11,12-benzo-1,4,7,10,13,16-hexaoxacyclooctadeca-11-ene)-4-O-[2-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyloxy)-ethane-1-yl]-2,3,6-trideoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of ethoxy-linked pseudo-disaccharides incorporating a crown ether macrocycle and lectin recognition

  摘要：

  Six ethoxy-linked pseudo-disaccharides incorporating a non-reducing D-galactopyranosyl residue and a glucose bearing an 18-crown-6-ether were synthesized by the trichloracetimidate method. Deprotection left four novel structures from which two were tested against the galactose-specific lectin Kluyveromyces bulgaricus. Their minimum inhibitory concentration (MIC) was in the same order of magnitude as compared to previously prepared oligosaccharides without spacer. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00194-9
• 作为产物：
  描述：

  methyl 4-O-allyl-[2,3-b](11,12-benzo-1,4,7,10,13,16-hexaoxacyclooctadeca-11-ene)-6-bromo-2,3,6-trideoxy-α-D-glucopyranoside 在 sodium azide 、 臭氧 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 methyl 6-azido-[2,3-b](11,12-benzo-1,4,7,10,13,16-hexaoxacyclooctadeca-11-ene)-4-O-(2-hydroxy-ethane-1-yl)-2,3,6-trideoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of ethoxy-linked pseudo-disaccharides incorporating a crown ether macrocycle and lectin recognition

  摘要：

  Six ethoxy-linked pseudo-disaccharides incorporating a non-reducing D-galactopyranosyl residue and a glucose bearing an 18-crown-6-ether were synthesized by the trichloracetimidate method. Deprotection left four novel structures from which two were tested against the galactose-specific lectin Kluyveromyces bulgaricus. Their minimum inhibitory concentration (MIC) was in the same order of magnitude as compared to previously prepared oligosaccharides without spacer. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00194-9