(2S,3S)-2-((2S,3R,4S,5S,6R)-4-Carboxymethoxy-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-3-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-succinic acid dimethyl ester | 181045-93-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S,3S)-2-((2S,3R,4S,5S,6R)-4-Carboxymethoxy-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-3-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-succinic acid dimethyl ester
• CAS: 181045-93-2
• 化学式: C₂₀H₃₂O₁₇
• 分子量: 544.464
• InChiKey: AUODILWEMANDEG-FBAYDUCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.16
• 重原子数：
  37.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  257.43
• 氢给体数：
  7.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  (2S,3S)-2-((2S,3R,4S,5S,6R)-4-Carboxymethoxy-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-3-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-succinic acid dimethyl ester 在 lithium hydroxide 作用下， 以 甲醇 为溶剂， 以84%的产率得到(2S,3S)-2-((2S,3R,4S,5S,6R)-4-Carboxymethoxy-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-3-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-succinic acid
  参考文献：
  名称：

  Mimics of the sialyl Lewis X tetrasaccharide. Replacement of the N-Acetylglucosamine sugar with simple C2-symmetric 1,2-diols

  摘要：

  Analogues of sialyl Lewis X have been synthesized that feature replacement of the N-acetylglucosamine residue with C-2-symmetric diols. The diols used contain different levels of torsional constraint and various functional groups. The cyclohexyl derived compound 27 was equipotent to sLex in vitro (IC50 0.5 mM). Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00055-7
• 作为产物：
  描述：

  ((2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methylsulfanyl-tetrahydro-pyran-4-yloxy)-acetic acid 在 palladium on activated charcoal N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 、 氢气 、 sodium hydride 作用下， 以 1,4-二氧六环 、 乙醇 、 乙腈 为溶剂， 反应 3.0h， 生成 (2S,3S)-2-((2S,3R,4S,5S,6R)-4-Carboxymethoxy-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-3-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-succinic acid dimethyl ester
  参考文献：
  名称：

  Mimics of the sialyl Lewis X tetrasaccharide. Replacement of the N-Acetylglucosamine sugar with simple C2-symmetric 1,2-diols

  摘要：

  Analogues of sialyl Lewis X have been synthesized that feature replacement of the N-acetylglucosamine residue with C-2-symmetric diols. The diols used contain different levels of torsional constraint and various functional groups. The cyclohexyl derived compound 27 was equipotent to sLex in vitro (IC50 0.5 mM). Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00055-7