(4aS,5R,7R,8R,8aS)-8-Benzyloxy-5-benzyloxymethyl-7-[2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-ethoxy]-tetrahydro-pyrano[3,4-b][1,4]dioxin-3-one | 163400-65-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4aS,5R,7R,8R,8aS)-8-Benzyloxy-5-benzyloxymethyl-7-[2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-ethoxy]-tetrahydro-pyrano[3,4-b][1,4]dioxin-3-one
• 英文别名: (4aS,5R,7R,8R,8aS)-7-[2-[(2R,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxyethoxy]-8-phenylmethoxy-5-(phenylmethoxymethyl)-5,7,8,8a-tetrahydro-4aH-pyrano[3,4-b][1,4]dioxin-3-one
• CAS: 163400-65-5
• 化学式: C₅₁H₅₆O₁₂
• 分子量: 860.998
• InChiKey: VPQLAGSQYKJGCK-VSXXEJLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  63
• 可旋转键数：
  21
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  119
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (4aS,5R,7R,8R,8aS)-8-Benzyloxy-5-benzyloxymethyl-7-[2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-ethoxy]-tetrahydro-pyrano[3,4-b][1,4]dioxin-3-one 在 palladium dihydroxide sodium hydroxide 、 氢气 作用下， 生成 Sodium; {(2R,3S,4S,5R,6R)-3,5-dihydroxy-2-hydroxymethyl-6-[2-((2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-ethoxy]-tetrahydro-pyran-4-yloxy}-acetate
  参考文献：
  名称：

  Synthesis of Biologically Active Sialyl Lewis X Mimetics

  摘要：

  The design and synthesis of two sialyl Lewis X (SLe(x)) mimetics are described. In the design of mimetic 1, an ethylene glycol linkage is used to bridge the fucose and galactose moiety, and a carboxymethyl group is placed in the 3-OH position of the galactose residue to provide the negative charge which is believed to be essential for binding to (E)-selectin. In the design of mimetic 2, a D-tartaric acid derivative is used to provide the trans-dihydroxyl groups originally from the glucosamine moiety for the linkage of the fucose and the carboxypentyl groups. At a concentration of 1.5 mM, 1 inhibits 50% of the binding of SLe(x) glycoconjugate to immobilized recombinant (E)-selectin, while 2 has an IC50 of 10 mM. Mimetic 1 is also found to be stable toward alpha-L-fucosidase. Results from the ROESY and COSY experiments indicate that compound 1 is conformationally flexible, which may explain its relatively weak activity compared to SLe(x) (IC50 = 0.8 mM).

  DOI：

  10.1021/jo00115a027
• 作为产物：
  描述：

  2,3,4-三-O-苄基-L-吡喃岩藻糖基氟化物 、 (4aS,5R,7R,8R,8aS)-8-Benzyloxy-5-benzyloxymethyl-7-(2-hydroxy-ethoxy)-tetrahydro-pyrano[3,4-b][1,4]dioxin-3-one 在 4 A molecular sieve 、 silver perchlorate 、 1,1,3,3-四甲基脲 、 tin(ll) chloride 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 (4aS,5R,7R,8R,8aS)-8-Benzyloxy-5-benzyloxymethyl-7-[2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-ethoxy]-tetrahydro-pyrano[3,4-b][1,4]dioxin-3-one 、 (4aS,5R,7R,8R,8aS)-8-Benzyloxy-5-benzyloxymethyl-7-[2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-ethoxy]-tetrahydro-pyrano[3,4-b][1,4]dioxin-3-one
  参考文献：
  名称：

  Synthesis of Biologically Active Sialyl Lewis X Mimetics

  摘要：

  The design and synthesis of two sialyl Lewis X (SLe(x)) mimetics are described. In the design of mimetic 1, an ethylene glycol linkage is used to bridge the fucose and galactose moiety, and a carboxymethyl group is placed in the 3-OH position of the galactose residue to provide the negative charge which is believed to be essential for binding to (E)-selectin. In the design of mimetic 2, a D-tartaric acid derivative is used to provide the trans-dihydroxyl groups originally from the glucosamine moiety for the linkage of the fucose and the carboxypentyl groups. At a concentration of 1.5 mM, 1 inhibits 50% of the binding of SLe(x) glycoconjugate to immobilized recombinant (E)-selectin, while 2 has an IC50 of 10 mM. Mimetic 1 is also found to be stable toward alpha-L-fucosidase. Results from the ROESY and COSY experiments indicate that compound 1 is conformationally flexible, which may explain its relatively weak activity compared to SLe(x) (IC50 = 0.8 mM).

  DOI：

  10.1021/jo00115a027

文献信息

• Synthesis of Biologically Active Sialyl Lewis X Mimetics
  作者：Hongmei Huang、Chi-Huey Wong

  DOI：10.1021/jo00115a027

  日期：1995.5

  The design and synthesis of two sialyl Lewis X (SLe(x)) mimetics are described. In the design of mimetic 1, an ethylene glycol linkage is used to bridge the fucose and galactose moiety, and a carboxymethyl group is placed in the 3-OH position of the galactose residue to provide the negative charge which is believed to be essential for binding to (E)-selectin. In the design of mimetic 2, a D-tartaric acid derivative is used to provide the trans-dihydroxyl groups originally from the glucosamine moiety for the linkage of the fucose and the carboxypentyl groups. At a concentration of 1.5 mM, 1 inhibits 50% of the binding of SLe(x) glycoconjugate to immobilized recombinant (E)-selectin, while 2 has an IC50 of 10 mM. Mimetic 1 is also found to be stable toward alpha-L-fucosidase. Results from the ROESY and COSY experiments indicate that compound 1 is conformationally flexible, which may explain its relatively weak activity compared to SLe(x) (IC50 = 0.8 mM).