methyl (2S,4S,5R,6R)-5-acetamido-4-acetyloxy-2-[(2R,3S,4S,5R,6S)-3,5-diacetyloxy-2-(acetyloxymethyl)-6-[(2R,3S,4R,5R)-2-(acetyloxymethyl)-6-chloro-5-(naphthalene-2-carbonylamino)-4-[(2S,3S,4R,5R,6S)-3,4,5-triacetyloxy-6-methyloxan-2-yl]oxyoxan-3-yl]oxyoxan-4-yl]oxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate | 180635-15-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (2S,4S,5R,6R)-5-acetamido-4-acetyloxy-2-[(2R,3S,4S,5R,6S)-3,5-diacetyloxy-2-(acetyloxymethyl)-6-[(2R,3S,4R,5R)-2-(acetyloxymethyl)-6-chloro-5-(naphthalene-2-carbonylamino)-4-[(2S,3S,4R,5R,6S)-3,4,5-triacetyloxy-6-methyloxan-2-yl]oxyoxan-3-yl]oxyoxan-4-yl]oxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 180635-15-8
• 化学式: C₆₃H₇₉ClN₂O₃₃
• 分子量: 1427.77
• InChiKey: GWCWOTOSERYEBM-QSLSEPMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  99
• 可旋转键数：
  38
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  438
• 氢给体数：
  2
• 氢受体数：
  33

反应信息

• 作为反应物：
  描述：

  1,3-苯二甲醇 、 methyl (2S,4S,5R,6R)-5-acetamido-4-acetyloxy-2-[(2R,3S,4S,5R,6S)-3,5-diacetyloxy-2-(acetyloxymethyl)-6-[(2R,3S,4R,5R)-2-(acetyloxymethyl)-6-chloro-5-(naphthalene-2-carbonylamino)-4-[(2S,3S,4R,5R,6S)-3,4,5-triacetyloxy-6-methyloxan-2-yl]oxyoxan-3-yl]oxyoxan-4-yl]oxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate 在 tin(II) trifluoromethanesulfonate 、 MS 4 Angstroem 、 1,1,3,3-四甲基脲 作用下， 以 二氯甲烷 为溶剂， 以11%的产率得到
  参考文献：
  名称：

  Synthesis and inhibitory effects of bivalent sialyl lewis X analogs at preventing cell adhesion

  摘要：

  Several sialyl Lewis X (SLeX) dimers attached to symmetric linkers, 1,3-di(omega-hydroxyalkyl)benzene, 1,3-di(omega-hydroxyalkoxy)benzene, and 1,3-di(omega-hydroxyalkoxy)cyclohexane, were synthesized and evaluated for their inhibitory activity against adhesion of HL-60 cells to recombinant soluble E-selectin. The SLeX dimers showed 4 to 6-fold higher inhibitory activity than the corresponding monomers. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00156-x
• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl -(2->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-O-<2,3,4-tri-O-acetyl-α-L-fucopyranosyl-(1->3)-O>-<6-O-acet... 在 1,1-二氯甲醚 、 zinc(II) chloride 作用下， 以 氯仿 为溶剂， 反应 6.0h， 生成 methyl (2S,4S,5R,6R)-5-acetamido-4-acetyloxy-2-[(2R,3S,4S,5R,6S)-3,5-diacetyloxy-2-(acetyloxymethyl)-6-[(2R,3S,4R,5R)-2-(acetyloxymethyl)-6-chloro-5-(naphthalene-2-carbonylamino)-4-[(2S,3S,4R,5R,6S)-3,4,5-triacetyloxy-6-methyloxan-2-yl]oxyoxan-3-yl]oxyoxan-4-yl]oxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
  参考文献：
  名称：

  SLeX类似物的便捷高效合成。

  摘要：

  描述了四糖1的制备和使用，其能够快速和制备规模地合成具有1-O-和2-N-二取代的葡糖胺（GlcN）部分的唾液酸化的路易斯X（SLeX）类似物。此类修饰应使SLeX类似物的物理和药理特性发生巨大变化。因此，四糖1是合成各种SLeX类似物的便利中间体，因为它具有可转换的2-（三甲基甲硅烷基）乙基（SE）糖苷和GlcN部分上的游离氨基。中间体1由葡糖胺衍生物通过酶促半乳糖基化/唾液酸化和化学岩藻糖基化的高效组合使用而构建。这样获得的1通过N-取代被转化为SLeX类似物，然后将SE糖苷转化为其他糖苷并脱保护。

  DOI：

  10.1021/jo960125f

文献信息

• Synthesis and inhibitory effect of a sialyl lewis X-acrylamide homopolymer at preventing cell adhesion
  作者：Hiroshi Miyauchi、Masashi Tanaka、Haruhiko Koike、Nobuko Kawamura、Masaji Hayashi

  DOI：10.1016/s0960-894x(97)00155-8

  日期：1997.4

  A novel glycopolymer, a homopolymer of conjugated SLeX-acrylamide, was synthesized and evaluated for its inhibitory activity against E-selectin mediated cell adhesion both in vitro and in vivo. The homopolymer showed approximately 10-fold higher activity per SLeX unit than the corresponding SLeX-acrylamide monomer in vitro and was significantly more effective in an LTA-induced murine pleurisy model. (C) 1997 Elsevier Science Ltd.