1,2-dioctanoyl-3-(N-octanoyl-6'-amino-6'-deoxy-α-D-mannopyranosyl)-sn-glycerol | 1473360-28-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 1,2-dioctanoyl-3-(N-octanoyl-6'-amino-6'-deoxy-α-D-mannopyranosyl)-sn-glycerol
• 英文别名: [(2S)-2-octanoyloxy-3-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-[(octanoylamino)methyl]oxan-2-yl]oxypropyl] octanoate
• CAS: 1473360-28-9
• 化学式: C₃₃H₆₁NO₁₀
• 分子量: 631.848
• InChiKey: NTXWOWBDJDQNQO-HJNNJASSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  44
• 可旋转键数：
  28
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  161
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  1,2,3,4-tetra-O-acetyl-6-azido-6-deoxy-α-D-mannopyranose 在 吡啶 、 甲醇 、 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 三氟甲磺酸三甲基硅酯 、 三氟化硼乙醚 、 水 、 氢气 、 sodium methylate 、 palladium(II) hydroxide 、 sodium hydride 、 对甲苯磺酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 异丙醇 、 丙酮 为溶剂， 反应 37.17h， 生成 1,2-dioctanoyl-3-(N-octanoyl-6'-amino-6'-deoxy-α-D-mannopyranosyl)-sn-glycerol
  参考文献：
  名称：

  Synthesis and antiviral evaluation of 6′-acylamido-6′-deoxy-α-d-mannoglycerolipids

  摘要：

  Eight new aminomannoglycerolipids (2a-h) with linear, branched, or aromatic acyl chains were synthesized and evaluated for their anti-influenza A virus (IAV) activity. By comparing six mannosyl donors with different protecting and leaving groups, the critical glycosylation reaction employed mannosyl trichloroacetimidate with 2-O-benzoyl protecting group as the donor to give the glycoside with absolute alpha-anomeric selectivity. The bioactivity results showed that the branched compound 2g could effectively inhibit IAV multiplication in MDCK cells with IC50 69.9 mu M. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.08.010

文献信息

• Synthesis and antiviral evaluation of 6′-acylamido-6′-deoxy-α-d-mannoglycerolipids
  作者：Jun Zhang、Yihua Sun、Wei Wang、Xiaoshuang Zhang、Chunxia Li、Huashi Guan

  DOI：10.1016/j.carres.2013.08.010

  日期：2013.11

  Eight new aminomannoglycerolipids (2a-h) with linear, branched, or aromatic acyl chains were synthesized and evaluated for their anti-influenza A virus (IAV) activity. By comparing six mannosyl donors with different protecting and leaving groups, the critical glycosylation reaction employed mannosyl trichloroacetimidate with 2-O-benzoyl protecting group as the donor to give the glycoside with absolute alpha-anomeric selectivity. The bioactivity results showed that the branched compound 2g could effectively inhibit IAV multiplication in MDCK cells with IC50 69.9 mu M. (C) 2013 Elsevier Ltd. All rights reserved.