[(2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-((2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-acetic acid methyl ester | 183954-71-4

• 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,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-((2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-acetic acid methyl ester
• 英文别名: methyl 2-[(2R,3S,4S,5R,6S)-3,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-[(2R,3S,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxan-4-yl]oxyacetate
• CAS: 183954-71-4
• 化学式: C₆₄H₆₈O₁₃
• 分子量: 1045.24
• InChiKey: QOWMGUWVWKPGIA-OQNSEIMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  77
• 可旋转键数：
  29
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  128
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  [(2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-((2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-acetic acid methyl ester 在 palladium dihydroxide 氢气 作用下， 以 甲醇 为溶剂， 生成 [(2R,3S,4S,5R,6S)-3,5-Dihydroxy-2-hydroxymethyl-6-((2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-acetic acid methyl ester
  参考文献：
  名称：

  Rational Design and Synthesis of a 1,1-Linked Disaccharide That Is 5 Times as Active as Sialyl Lewis X in Binding to E-Selectin

  摘要：

  We describe here a rational design and synthesis of (3-O-carboxymethyl)-beta-D-galactopyranosyl alpha-D-mannopyranoside which is 5 times as active as sialyl Lewis X in binding to E-selectin and also effective against P- and L-selectin. A new method for the 1,1-glycosidic bond formation via coupling of protected trimethylsilyl beta-D-galactoside and alpha-mannosyl fluoride in the presence of BF3 . Et(2)O is described.

  DOI：

  10.1021/ja9611093
• 作为产物：
  描述：

  2,4,6-tri-O-benzyl-3-O-(4-methoxybenzyl)-D-galactopyranose 在 吡啶 、 甲醇 、 三氟化硼乙醚 、 sodium methylate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 potassium iodide 、 silver(l) oxide 作用下， 以 二氯甲烷 、 氯仿 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 111.3h， 生成 [(2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-((2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-acetic acid methyl ester
  参考文献：
  名称：

  Rational Design and Synthesis of a 1,1-Linked Disaccharide That Is 5 Times as Active as Sialyl Lewis X in Binding to E-Selectin

  摘要：

  We describe here a rational design and synthesis of (3-O-carboxymethyl)-beta-D-galactopyranosyl alpha-D-mannopyranoside which is 5 times as active as sialyl Lewis X in binding to E-selectin and also effective against P- and L-selectin. A new method for the 1,1-glycosidic bond formation via coupling of protected trimethylsilyl beta-D-galactoside and alpha-mannosyl fluoride in the presence of BF3 . Et(2)O is described.

  DOI：

  10.1021/ja9611093

文献信息

• Rational Design and Synthesis of a 1,1-Linked Disaccharide That Is 5 Times as Active as Sialyl Lewis X in Binding to E-Selectin
  作者：Kazumi Hiruma、Tetsuya Kajimoto、Gabriel Weitz-Schmidt、Ian Ollmann、Chi-Huey Wong

  DOI：10.1021/ja9611093

  日期：1996.1.1

  We describe here a rational design and synthesis of (3-O-carboxymethyl)-beta-D-galactopyranosyl alpha-D-mannopyranoside which is 5 times as active as sialyl Lewis X in binding to E-selectin and also effective against P- and L-selectin. A new method for the 1,1-glycosidic bond formation via coupling of protected trimethylsilyl beta-D-galactoside and alpha-mannosyl fluoride in the presence of BF3 . Et(2)O is described.