O-(4-O-Acetyl-2,6-di-O-benzoyl-3-O-levulinyl-β-D-galactopyranosyl)-(1->4)-O-<(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1->3)>-2,6-di-O-benzoyl-β-D-glucopyranosyltrichloroacetimidate | 165621-44-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: O-(4-O-Acetyl-2,6-di-O-benzoyl-3-O-levulinyl-β-D-galactopyranosyl)-(1->4)-O-<(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1->3)>-2,6-di-O-benzoyl-β-D-glucopyranosyltrichloroacetimidate
• 英文别名: [(2R,3R,4S,5R,6R)-3-[(2S,3R,4S,5S,6R)-5-acetyloxy-3-benzoyloxy-6-(benzoyloxymethyl)-4-(4-oxopentanoyloxy)oxan-2-yl]oxy-5-benzoyloxy-4-[(2S,3S,4R,5R,6S)-3,4,5-triacetyloxy-6-methyloxan-2-yl]oxy-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methyl benzoate
• CAS: 165621-44-3
• 化学式: C₆₁H₆₂Cl₃NO₂₅
• 分子量: 1315.51
• InChiKey: IPZIPPZBCGJGKI-XTDSMSNBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  90
• 可旋转键数：
  33
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  333
• 氢给体数：
  1
• 氢受体数：
  26

反应信息

• 作为反应物：
  描述：

  2-tetradecylhexadecan-1-ol 、 O-(4-O-Acetyl-2,6-di-O-benzoyl-3-O-levulinyl-β-D-galactopyranosyl)-(1->4)-O-<(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1->3)>-2,6-di-O-benzoyl-β-D-glucopyranosyltrichloroacetimidate 在 4 A molecular sieve 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以69%的产率得到2-(Tetradecyl)hexadecyl O-(4-O-acetyl-2,6-di-O-benzoyl-3-O-levulinyl-β-D-galactopyranosyl)-(1->4)-O-<(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1->3)>-2,6-di-O-benzoyl-β-D-glucopyranoside
  参考文献：
  名称：

  Hasegawa, Akira; Ito, Kenichi; Ishida, Hideharu, Journal of Carbohydrate Chemistry, 1995, vol. 14, # 3, p. 353 - 368

  摘要：

  DOI：
• 作为产物：
  描述：

  三氯乙腈 、 O-(4-O-Acetyl-2,6-di-O-benzoyl-3-O-levulinyl-β-D-galactopyranosyl)-(1->4)-O-<(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1->3)>-O-2,6-di-O-benzoyl-β-D-glucopyranose 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以95%的产率得到O-(4-O-Acetyl-2,6-di-O-benzoyl-3-O-levulinyl-β-D-galactopyranosyl)-(1->4)-O-<(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1->3)>-2,6-di-O-benzoyl-β-D-glucopyranosyltrichloroacetimidate
  参考文献：
  名称：

  Hasegawa, Akira; Ito, Kenichi; Ishida, Hideharu, Journal of Carbohydrate Chemistry, 1995, vol. 14, # 3, p. 353 - 368

  摘要：

  DOI：

文献信息

• Studies on Selectin Blockers. 2. Novel Selectin Blocker as Potential Therapeutics for Inflammatory Disorders
  作者：Yukihisa Wada、Tadayuki Saito、Naomi Matsuda、Hiroshi Ohmoto、Kohichiro Yoshino、Masami Ohashi、Hirosato Kondo、Hideharu Ishida、Makoto Kiso、Akira Hasegawa

  DOI：10.1021/jm950877m

  日期：1996.1.1

  As a part of our studies of selectin blockers, we prepared 1-(2-tetradecylhexadecyl)-3'-O-sulfo Le(X) 1 and 1-(2-tetradecylhexadecyl) sLe(X) 2 and examined their inhibitory activities against natural ligand (sLe(X)) binding to E-, P-, and L-selectins. Compounds 1 and 2 were 2 times more potent than the sLe(X) tetrasaccharide toward E-selectin binding and up to 4 times more potent than sLe(X) toward P- and L-selectin binding. Interestingly, compound 1 provided dose-dependent protective effects against an immunoglobulin E-mediated skin reaction in mouse ears. This protective effect was associated with diminished tissue accumulation of neutrophils in the ear (as assessed by myeloperoxidase). These findings indicate that the modification of sLe(X) or 3'-O-sulfo Le(X) with a ''branched anchor'', a 2-tetradecylhexadecyl group, is useful in the design of a more potent selectin blocker, which has broad inhibitory activities toward all selectins.