Bn(-2)[Mob(-3)][Bn(-4)][Bn(-6)]Gal(b)-O-TMS | 183954-72-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Bn(-2)[Mob(-3)][Bn(-4)][Bn(-6)]Gal(b)-O-TMS
• 英文别名: [(2S,3R,4S,5S,6R)-4-[(4-methoxyphenyl)methoxy]-3,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-trimethylsilane
• CAS: 183954-72-5
• 化学式: C₃₈H₄₆O₇Si
• 分子量: 642.865
• InChiKey: VYFKLNCCTBBNDZ-LDVAZLSXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.54
• 重原子数：
  46
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Bn(-2)[Mob(-3)][Bn(-4)][Bn(-6)]Gal(b)-O-TMS 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 作用下， 以 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 22.5h， 生成 2,4,6-tri-O-benzyl-β-D-galactopyranosyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside
  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：

  三甲基硅烷基二乙胺 、 2,4,6-tri-O-benzyl-3-O-(4-methoxybenzyl)-D-galactopyranose 以 甲苯 为溶剂， 生成 Bn(-2)[Mob(-3)][Bn(-4)][Bn(-6)]Gal(b)-O-TMS
  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.