1,2-dilauroyl-3-(N-lauroyl-6'-amino-6'-deoxy-α-D-galactosyl)-sn-glycerol

• 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-dilauroyl-3-(N-lauroyl-6'-amino-6'-deoxy-α-D-galactosyl)-sn-glycerol
• 英文别名: [(2S)-3-[(2S,3R,4S,5R,6R)-6-[(dodecanoylamino)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy-2-dodecanoyloxypropyl] dodecanoate
• 化学式: C₄₅H₈₅NO₁₀
• 分子量: 800.171
• InChiKey: BPTGJZIVXBWEOX-DPQOLWQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.3
• 重原子数：
  56
• 可旋转键数：
  40
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 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：

  p-tolyl 2,3,4-tri-O-benzyl-1-thio-β-D-galactopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 sodium azide 、 三氟甲磺酸三甲基硅酯 、 10% palladium hydroxide on charcoal 、 水 、 氢气 、 对甲苯磺酸 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 异丙醇 、 丙酮 为溶剂， 反应 28.5h， 生成 1,2-dilauroyl-3-(N-lauroyl-6'-amino-6'-deoxy-α-D-galactosyl)-sn-glycerol
  参考文献：
  名称：

  Synthesis of 6′-acylamido-6′-deoxy-α-d-galactoglycerolipids

  摘要：

  Aminoglycoglycerolipid 1a isolated from an algal extract showed activity against the enzyme Myt1 kinase with an IC50 value of 0.12 mu g/mL. Its analogues, 6'-acylamido-6'-deoxy-alpha-D-galactoglycerolipids (2a-g) were synthesized in an efficient way with high stereoselectivity. The key step was to employ a 4-OAc protecting group of the galactosyl donor 14 as a remote neighboring participation group to give the glycoside with high alpha-anomeric selectivity (alpha:beta = 32:1) in the glycosylation. The preliminary bioactivity screening showed that compound 2g exhibited good inhibition against Myt1 kinase. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.02.008

文献信息

• Synthesis of 6′-acylamido-6′-deoxy-α-d-galactoglycerolipids
  作者：Chunxia Li、Yihua Sun、Jun Zhang、Zhimin Zhao、Guangli Yu、Huashi Guan

  DOI：10.1016/j.carres.2013.02.008

  日期：2013.7

  Aminoglycoglycerolipid 1a isolated from an algal extract showed activity against the enzyme Myt1 kinase with an IC50 value of 0.12 mu g/mL. Its analogues, 6'-acylamido-6'-deoxy-alpha-D-galactoglycerolipids (2a-g) were synthesized in an efficient way with high stereoselectivity. The key step was to employ a 4-OAc protecting group of the galactosyl donor 14 as a remote neighboring participation group to give the glycoside with high alpha-anomeric selectivity (alpha:beta = 32:1) in the glycosylation. The preliminary bioactivity screening showed that compound 2g exhibited good inhibition against Myt1 kinase. (C) 2013 Elsevier Ltd. All rights reserved.