3-O-(6'-amino-2',3',4'-tri-O-benzyl-6'-deoxy-α-D-glucopyranosyl)-sn-glycerol | 1383450-05-2

• 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: 3-O-(6'-amino-2',3',4'-tri-O-benzyl-6'-deoxy-α-D-glucopyranosyl)-sn-glycerol
• 英文别名: (2R)-3-[(2S,3R,4S,5R,6R)-6-(aminomethyl)-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxypropane-1,2-diol
• CAS: 1383450-05-2
• 化学式: C₃₀H₃₇NO₇
• 分子量: 523.626
• InChiKey: ONHNRKXQZADWBB-XFKPVUIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  38
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-O-(6'-amino-2',3',4'-tri-O-benzyl-6'-deoxy-α-D-glucopyranosyl)-sn-glycerol 在 4-二甲氨基吡啶 、 20 % Pd(OH)2/C 、 氢气 作用下， 以 四氢呋喃 、 吡啶 、 异丙醇 为溶剂， 反应 10.0h， 生成 1,2-dioctanoyl-3-(N-octeoyl-6'-amino-6'-deoxy-α-D-glucopyranosyl)-sn-glycerol
  参考文献：
  名称：

  Synthesis of glycoglycerolipid of 1,2-dipalmitoyl-3-(N-palmitoyl-6′-amino-6′-deoxy-α-d-glucosyl)-sn-glycerol and its analogues, inhibitors of human Myt1-kinase

  摘要：

  A glycoglycerolipid 1a isolated from a marine alga showed inhibition to Myt1 kinase with IC50 of 0.12 mu g/mL. We synthesized 1a and its seven analogues (1b-h) in an efficient method with high stereoselectivity. The process employed trichloroacetimidate donor 4b at low substrate concentration to achieve high alpha-selectivity (alpha/beta = 33: 1) in glycosylation reaction. The present synthesis provided various acyl derivatives required for the study on the structure-activity relationship later. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.04.005
• 作为产物：
  描述：

  6-azido-2,3,4-tri-O-benzyl-6-deoxy-α-D-glucopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 、 对甲苯磺酸 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 水 为溶剂， 反应 7.5h， 生成 3-O-(6'-amino-2',3',4'-tri-O-benzyl-6'-deoxy-α-D-glucopyranosyl)-sn-glycerol
  参考文献：
  名称：

  Synthesis of glycoglycerolipid of 1,2-dipalmitoyl-3-(N-palmitoyl-6′-amino-6′-deoxy-α-d-glucosyl)-sn-glycerol and its analogues, inhibitors of human Myt1-kinase

  摘要：

  A glycoglycerolipid 1a isolated from a marine alga showed inhibition to Myt1 kinase with IC50 of 0.12 mu g/mL. We synthesized 1a and its seven analogues (1b-h) in an efficient method with high stereoselectivity. The process employed trichloroacetimidate donor 4b at low substrate concentration to achieve high alpha-selectivity (alpha/beta = 33: 1) in glycosylation reaction. The present synthesis provided various acyl derivatives required for the study on the structure-activity relationship later. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.04.005