1,2-di-O-isovaleryl-3-O-(N-isovaleryl-6'-amino-2',3',4'-tri-O-benzyl-6'-deoxy-α-D-glucopyranosyl)-sn-glycerol | 1383450-16-5

• 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-di-O-isovaleryl-3-O-(N-isovaleryl-6'-amino-2',3',4'-tri-O-benzyl-6'-deoxy-α-D-glucopyranosyl)-sn-glycerol
• CAS: 1383450-16-5
• 化学式: C₄₅H₆₁NO₁₀
• 分子量: 775.98
• InChiKey: DOQIRNSANHEDSV-IUWNLENJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.19
• 重原子数：
  56.0
• 可旋转键数：
  23.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  127.85
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  1,2-di-O-isovaleryl-3-O-(N-isovaleryl-6'-amino-2',3',4'-tri-O-benzyl-6'-deoxy-α-D-glucopyranosyl)-sn-glycerol 在 20 % Pd(OH)2/C 、 氢气 作用下， 以 四氢呋喃 、 异丙醇 为溶剂， 反应 6.0h， 以88%的产率得到1,2-di-O-isovaleryl-3-O-(N-isovaleryl-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：

  3-O-(6'-azido-2',3',4'-tri-O-benzyl-6'-deoxy-α-D-glucosyl)-sn-glycerol 在 4-二甲氨基吡啶 、 三苯基膦 作用下， 以 四氢呋喃 、 吡啶 、 水 为溶剂， 反应 9.0h， 生成 1,2-di-O-isovaleryl-3-O-(N-isovaleryl-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