Acetic acid (2R,3S,4S,5R,6S)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-trimethylsilanyloxy-tetrahydro-pyran-4-yl ester | 183954-65-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2R,3S,4S,5R,6S)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-trimethylsilanyloxy-tetrahydro-pyran-4-yl ester
• 英文别名: Bn(-2)[Bn(-4)][Bn(-6)]Gal3Ac(b)-O-TMS；[(2R,3S,4S,5R,6S)-3,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-trimethylsilyloxyoxan-4-yl] acetate
• CAS: 183954-65-6
• 化学式: C₃₂H₄₀O₇Si
• 分子量: 564.751
• InChiKey: JICXFWWGBTZGAO-MQSWGENCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.88
• 重原子数：
  40
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3S,4S,5R,6S)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-trimethylsilanyloxy-tetrahydro-pyran-4-yl ester 在 甲醇 、 三氟化硼乙醚 、 sodium methylate 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 21.5h， 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：

  2,4,6-tri-O-benzyl-3-O-(4-methoxybenzyl)-D-galactopyranose 在 吡啶 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 1.0h， 生成 Acetic acid (2R,3S,4S,5R,6S)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-trimethylsilanyloxy-tetrahydro-pyran-4-yl 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

• Synthesis of analogs of 1,1-linked galactosyl mannoside as mimetics of sialyl Lewis X tetrasaccharide
  作者：Kazumi Hiruma、Osamu Kanie、Chi-Huey Wong

  DOI：10.1016/s0040-4020(98)00990-9

  日期：1998.12

  for the incorporation of hydrophobic groups with and without positive or negative charge to position-6 of the mannose residue in the 1,1-linked disaccharide as mimetics of sialyl Lewis X tetrasaccharide in order to enhance binding affinity to selectins.

  已经开发了将带有或不带正电荷或不带正电荷或不带正电荷的疏水基团掺入到1，1-连接的二糖中的甘露糖残基的6位上的方法，以作为唾液酸路易斯X四糖的模拟物，以增强与选择素的结合亲和力。