methyl (2S)-3-[(2S,3R,4R,5R,6R)-3-acetamido-6-[[(2R,3R,4R,5S,6R)-3-acetamido-4-acetyloxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]oxymethyl]-4,5-diacetyloxyoxan-2-yl]oxy-2-(phenylmethoxycarbonylamino)propanoate | 729602-88-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (2S)-3-[(2S,3R,4R,5R,6R)-3-acetamido-6-[[(2R,3R,4R,5S,6R)-3-acetamido-4-acetyloxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]oxymethyl]-4,5-diacetyloxyoxan-2-yl]oxy-2-(phenylmethoxycarbonylamino)propanoate
• CAS: 729602-88-4
• 化学式: C₄₈H₆₅N₃O₂₇
• 分子量: 1116.05
• InChiKey: LTIWKVMUBSAWNV-WHODETJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  78
• 可旋转键数：
  32
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  383
• 氢给体数：
  4
• 氢受体数：
  27

反应信息

• 作为反应物：
  描述：

  methyl (2S)-3-[(2S,3R,4R,5R,6R)-3-acetamido-6-[[(2R,3R,4R,5S,6R)-3-acetamido-4-acetyloxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]oxymethyl]-4,5-diacetyloxyoxan-2-yl]oxy-2-(phenylmethoxycarbonylamino)propanoate 在 sodium methylate 作用下， 以 甲醇 、 水 为溶剂， 反应 30.0h， 以95%的产率得到3-{3-acetylamino-6-[3-acetylamino-4-hydroxy-6-hydroxymethyl-5-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxymethyl]-4,5-dihydroxy-tetrahydro-pyran-2-yloxy}-2-benzyloxycarbonylamino-propionic acid
  参考文献：
  名称：

  Syntheses of 6-Sulfo Sialyl Lewis X Glycans Corresponding to the l-Selectin Ligand “Sulfoadhesin”

  摘要：

  Divergent syntheses of sulfated sialyl Lewis X oligosaccharides corresponding to the core 1 and core 6 branches of the L-selectin ligand are reported. These synthetic targets incorporate a selectively protected serine residue at the reducing terminus, providing a functional handle for further conjugation.

  DOI：

  10.1021/ol0493195
• 作为产物：
  描述：

  phenyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-3-O-acetyl-6-O-t-butyldiphenylsilyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-glucopyranoside 在 吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 四丁基氟化铵 、 溶剂黄146 、 锌 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 75.5h， 生成 methyl (2S)-3-[(2S,3R,4R,5R,6R)-3-acetamido-6-[[(2R,3R,4R,5S,6R)-3-acetamido-4-acetyloxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]oxymethyl]-4,5-diacetyloxyoxan-2-yl]oxy-2-(phenylmethoxycarbonylamino)propanoate
  参考文献：
  名称：

  Syntheses of 6-Sulfo Sialyl Lewis X Glycans Corresponding to the l-Selectin Ligand “Sulfoadhesin”

  摘要：

  Divergent syntheses of sulfated sialyl Lewis X oligosaccharides corresponding to the core 1 and core 6 branches of the L-selectin ligand are reported. These synthetic targets incorporate a selectively protected serine residue at the reducing terminus, providing a functional handle for further conjugation.

  DOI：

  10.1021/ol0493195