3-O-(2,2',3,3',4',6,6'-Hepta-O-acetyl-β-D-maltosyl)-2-O-methyl-1-O-hexadecyl-sn-glycerol | 133777-41-0

• 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-(2,2',3,3',4',6,6'-Hepta-O-acetyl-β-D-maltosyl)-2-O-methyl-1-O-hexadecyl-sn-glycerol
• 英文别名: 1-O-hexadecyl-2-O-methyl-3-O-(2,3,6,2',3',4',6'-hepta-O-acetyl-β-D-maltosyl)-sn-glycerol；[(2R,3R,4S,5R,6R)-4,5-diacetyloxy-6-[(2R)-3-hexadecoxy-2-methoxypropoxy]-3-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 133777-41-0
• 化学式: C₄₆H₇₆O₂₀
• 分子量: 949.097
• InChiKey: RGMLDWFPRPNKBX-RMCUYQLUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  66
• 可旋转键数：
  39
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  240
• 氢给体数：
  0
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  3-O-(2,2',3,3',4',6,6'-Hepta-O-acetyl-β-D-maltosyl)-2-O-methyl-1-O-hexadecyl-sn-glycerol 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 以98%的产率得到1-O-Hexadecyl-3-O-β-D-maltosyl-2-O-methyl-sn-glycerol
  参考文献：
  名称：

  A Facile Stereoselective Synthesis of Ether-Linkedβ-D-Maltosyl- andβ-D-Lactosyl-glycerolipids via Peracetylated Disaccharideα-Phosphoramidates

  摘要：

  The reaction of 1-0-hexadecyl-2-O-methyl-sn-glycerol with 2,3,6,2',3',4',6'-hepta-O-acetyl-alpha-lactosylphosphoramidate or alpha-maltosylphosphoramidate in the presence of trimethylsilyl triflate and molecular sieves afforded 1-0-hexadecyl-2-0-methyl-3-0-(2,3,6,2',3',4',6'-hepta-0-acetyl-beta-lactosyl)-sn-glycerolipid or beta-maltosyl-sn-glycerolipid stereoselectively in moderate yields after column chromatography. Alkaline hydrolysis of the O-peracetyl glycerolipids gave the desired beta-glycolipids 1 and 2.

  DOI：

  10.1080/00397919408010593
• 作为产物：
  描述：

  十六基甲基甘油 、 2,3,6,2',3',4',6'-hepta-O-acetyl-α-D-maltosylphosphoramidate 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 以48%的产率得到3-O-(2,2',3,3',4',6,6'-Hepta-O-acetyl-β-D-maltosyl)-2-O-methyl-1-O-hexadecyl-sn-glycerol
  参考文献：
  名称：

  A Facile Stereoselective Synthesis of Ether-Linkedβ-D-Maltosyl- andβ-D-Lactosyl-glycerolipids via Peracetylated Disaccharideα-Phosphoramidates

  摘要：

  The reaction of 1-0-hexadecyl-2-O-methyl-sn-glycerol with 2,3,6,2',3',4',6'-hepta-O-acetyl-alpha-lactosylphosphoramidate or alpha-maltosylphosphoramidate in the presence of trimethylsilyl triflate and molecular sieves afforded 1-0-hexadecyl-2-0-methyl-3-0-(2,3,6,2',3',4',6'-hepta-0-acetyl-beta-lactosyl)-sn-glycerolipid or beta-maltosyl-sn-glycerolipid stereoselectively in moderate yields after column chromatography. Alkaline hydrolysis of the O-peracetyl glycerolipids gave the desired beta-glycolipids 1 and 2.

  DOI：

  10.1080/00397919408010593