(2,4,6-tri-O-benzyl-1-deoxy-1-methylsulfanyl-β-D-galactopyranos-3-yl)-acetic acid benzyl ester | 165557-04-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2,4,6-tri-O-benzyl-1-deoxy-1-methylsulfanyl-β-D-galactopyranos-3-yl)-acetic acid benzyl ester
• CAS: 165557-04-0
• 化学式: C₃₇H₄₀O₇S
• 分子量: 628.786
• InChiKey: KWNVSCNBYPAVOU-VCPMIQRASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.59
• 重原子数：
  45.0
• 可旋转键数：
  16.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  72.45
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (2,4,6-tri-O-benzyl-1-deoxy-1-methylsulfanyl-β-D-galactopyranos-3-yl)-acetic acid benzyl ester 在 palladium on activated charcoal N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 、 氢气 作用下， 以 1,4-二氧六环 、 乙醇 、 乙腈 为溶剂， 反应 1.0h， 生成 {(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：

  (1-deoxy-1-methylsulfanyl-β-D-galactopyranos-3-yl)-acetic acid tert-butyl ester 在 sodium hydride 、 溶剂黄146 作用下， 反应 2.0h， 生成 (2,4,6-tri-O-benzyl-1-deoxy-1-methylsulfanyl-β-D-galactopyranos-3-yl)-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 of a novel analogue of sialyl Lewis X
  作者：Jeremy C. Prodger、Mark J. Bamford、Paul M. Gore、Duncan S. Holmes、Victoria Saez、Peter Ward

  DOI：10.1016/0040-4039(95)00250-g

  日期：1995.3

  Two different strategies have been developed in order to synthesise an analogue and potential mimic of sialyl Lewis X that incorporates a carboxymethyl group and a C2-symmetric 2,3-butanediol unit as replacements for the sialic acid and the N-acetylglucosamine residues respectively.

  为了合成唾液酸路易斯X的类似物和潜在的模仿物，已经开发了两种不同的策略，其结合了羧甲基和C 2对称的2，3-丁二醇单元，分别取代了唾液酸和N-乙酰氨基葡糖残基。
• 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.