{(2R,3S,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-4-yloxy}-acetic acid benzyl ester | 175472-99-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: {(2R,3S,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-4-yloxy}-acetic acid benzyl ester
• CAS: 175472-99-8
• 化学式: C₆₉H₇₆O₁₃
• 分子量: 1113.35
• InChiKey: VVWHMIYNQHHWRS-KEGMJHHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.07
• 重原子数：
  82.0
• 可旋转键数：
  28.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  127.83
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  {(2R,3S,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-4-yloxy}-acetic acid benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 以80%的产率得到{(2R,3S,4S,5R,6R)-3,5-Dihydroxy-2-hydroxymethyl-6-[(1R,2R)-2-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-4-yloxy}-acetic 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 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 、 sodium hydride 作用下， 以 乙腈 为溶剂， 反应 3.0h， 生成 {(2R,3S,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-4-yloxy}-acetic acid benzyl 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

文献信息

• Synthesis and biological activity of conformationally constrained sialyl Lewis X analogues with reduced carbohydrate character
  作者：Mark J. Bamford、Michael Bird、Paul M. Gore、Duncan S. Holmes、Richard Priest、Jeremy C. Prodger、Victoria Saez

  DOI：10.1016/0960-894x(96)00008-x

  日期：1996.2

  Two conformationally constrained analogues of sialyl Lewis X have been synthesised in which the GlcNAc residue has been replaced with cyclohexyl and phenyl rings. The cyclohexyl derived compound was equipotent to sLex and sLea in vitro, suggesting the main role of the GlcNAc residue in sLex is conformational, and represents a simplified inhibitor of adhesion.