(2'R)-2',3'-di-hexadecyloxypropyl-O-<(3,4-O-isopropylidene)-2,6-di-O-sulfonyl>-β-D-galactopyranoside | 210221-87-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: (2'R)-2',3'-di-hexadecyloxypropyl-O-<(3,4-O-isopropylidene)-2,6-di-O-sulfonyl>-β-D-galactopyranoside
• 英文别名: [(3aS,4R,6R,7R,7aS)-6-[(2R)-2,3-dihexadecoxypropoxy]-2,2-dimethyl-7-sulfooxy-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl]methyl hydrogen sulfate
• CAS: 210221-87-7
• 化学式: C₄₄H₈₆O₁₄S₂
• 分子量: 903.29
• InChiKey: OPIYKNRBMOHLCX-AOXICKKISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.5
• 重原子数：
  60
• 可旋转键数：
  41
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  199
• 氢给体数：
  2
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  (2'R)-2',3'-di-hexadecyloxypropyl-O-<(3,4-O-isopropylidene)-2,6-di-O-sulfonyl>-β-D-galactopyranoside 在 三氟乙酸 作用下， 以 水 为溶剂， 反应 4.0h， 以88%的产率得到(2'R)-2',3'-di-hexadecyloxypropyl-O-(2,6-di-O-sulfonyl)-β-D-galactopyranoside
  参考文献：
  名称：

  Short synthesis of sulfatide- and SQDG-mimetics as small molecular weight selectin inhibitors

  摘要：

  Small molecular weight sulfatide analogs were synthesised and tested in cell-based selectin mediated adhesion assays. The ceramide moiety of sulfatides could be replaced by simple glycerol ethers to obtain potent mimetics. The specific activity of these inhibitors towards P-selectin is illustrated by analogy with other polyanionic systems forming polyvalent arrays antagonising the polyanionic N-terminal binding sites of the dimeric PSGL-1 ligand. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00950-8
• 作为产物：
  描述：

  1,2-o-二十六基-sn-甘油 在 三氟甲磺酸三甲基硅酯 、 sodium methylate 、 三氧化硫吡啶 、 对甲苯磺酸 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 23.5h， 生成 (2'R)-2',3'-di-hexadecyloxypropyl-O-<(3,4-O-isopropylidene)-2,6-di-O-sulfonyl>-β-D-galactopyranoside
  参考文献：
  名称：

  Short synthesis of sulfatide- and SQDG-mimetics as small molecular weight selectin inhibitors

  摘要：

  Small molecular weight sulfatide analogs were synthesised and tested in cell-based selectin mediated adhesion assays. The ceramide moiety of sulfatides could be replaced by simple glycerol ethers to obtain potent mimetics. The specific activity of these inhibitors towards P-selectin is illustrated by analogy with other polyanionic systems forming polyvalent arrays antagonising the polyanionic N-terminal binding sites of the dimeric PSGL-1 ligand. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00950-8

文献信息

• Short synthesis of sulfatide- and SQDG-mimetics as small molecular weight selectin inhibitors
  作者：Gerhard Kretzschmar、Alexander Toepfer、Michael Sonnentag

  DOI：10.1016/s0040-4020(98)00950-8

  日期：1998.12

  Small molecular weight sulfatide analogs were synthesised and tested in cell-based selectin mediated adhesion assays. The ceramide moiety of sulfatides could be replaced by simple glycerol ethers to obtain potent mimetics. The specific activity of these inhibitors towards P-selectin is illustrated by analogy with other polyanionic systems forming polyvalent arrays antagonising the polyanionic N-terminal binding sites of the dimeric PSGL-1 ligand. (C) 1998 Elsevier Science Ltd. All rights reserved.