1-((2S,3S,4R)-3,4-bis(4-methoxybenzyloxy)-1-((2S,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yloxy)octadecan-2-yl)-4-pentacosyl-1H-1,2,3-triazole

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 英文名称: 1-((2S,3S,4R)-3,4-bis(4-methoxybenzyloxy)-1-((2S,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yloxy)octadecan-2-yl)-4-pentacosyl-1H-1,2,3-triazole
• 英文别名: 1-[(2S,3S,4R)-3,4-bis[(4-methoxyphenyl)methoxy]-1-[(2S,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoctadecan-2-yl]-4-pentacosyltriazole
• 化学式: C₉₅H₁₃₉N₃O₁₀
• 分子量: 1483.16
• InChiKey: AIQROFJTWLPQNA-ZYHBKYQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  28
• 重原子数：
  108
• 可旋转键数：
  64
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  123
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  1-((2S,3S,4R)-3,4-bis(4-methoxybenzyloxy)-1-((2S,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yloxy)octadecan-2-yl)-4-pentacosyl-1H-1,2,3-triazole 在 palladium dihydroxide 氢气 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 以70%的产率得到(2S,3R,4S,5R,6R)-2-((2S,3S,4R)-3,4-dihydroxy-2-(4-pentacosyl-1H-1,2,3-triazol-1-yl)octadecyloxy)-6-(hydroxymethyl)-tetrahydro-2H-pyrane-3,4,5-triol
  参考文献：
  名称：

  Synthesis and Evaluation of 1,2,3-Triazole Containing Analogues of the Immunostimulant α-GalCer

  摘要：

  alpha-GalCer is the first defined and most potent agonistic antigen of the T cell receptor of natural killer T cells. We have prepared a series of 1,2,3-triazole-containing alpha-GalCer analogues in which the lipid chain lengths have been incrementally varied. We found that this isosteric replacement of alpha-GalCer's amide moiety with triazole increases the IL-4 versus IFN-gamma bias of released cytokines. The stimulatory effect was influenced by the length of the attached chain. In particular, the long-chained triazole analogues have a comparable stimulatory effect on cytokine production as alpha-GalCer and exhibit a stronger Th2 cytokine response.

  DOI：

  10.1021/jm061243q
• 作为产物：
  描述：

  (2S,3S,4R)-2-azido-3,4-di-O-para-methoxybenzyl-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-octadecane 、 1-heptacosyne 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 24.0h， 以73%的产率得到1-((2S,3S,4R)-3,4-bis(4-methoxybenzyloxy)-1-((2S,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yloxy)octadecan-2-yl)-4-pentacosyl-1H-1,2,3-triazole
  参考文献：
  名称：

  Synthesis and Evaluation of 1,2,3-Triazole Containing Analogues of the Immunostimulant α-GalCer

  摘要：

  alpha-GalCer is the first defined and most potent agonistic antigen of the T cell receptor of natural killer T cells. We have prepared a series of 1,2,3-triazole-containing alpha-GalCer analogues in which the lipid chain lengths have been incrementally varied. We found that this isosteric replacement of alpha-GalCer's amide moiety with triazole increases the IL-4 versus IFN-gamma bias of released cytokines. The stimulatory effect was influenced by the length of the attached chain. In particular, the long-chained triazole analogues have a comparable stimulatory effect on cytokine production as alpha-GalCer and exhibit a stronger Th2 cytokine response.

  DOI：

  10.1021/jm061243q

文献信息

• Synthesis and Evaluation of 1,2,3-Triazole Containing Analogues of the Immunostimulant α-GalCer
  作者：Taeho Lee、Minjae Cho、Sung-Youl Ko、Hyun-Jun Youn、Dong Jae Baek、Won-Jea Cho、Chang-Yuil Kang、Sanghee Kim

  DOI：10.1021/jm061243q

  日期：2007.2.8

  alpha-GalCer is the first defined and most potent agonistic antigen of the T cell receptor of natural killer T cells. We have prepared a series of 1,2,3-triazole-containing alpha-GalCer analogues in which the lipid chain lengths have been incrementally varied. We found that this isosteric replacement of alpha-GalCer's amide moiety with triazole increases the IL-4 versus IFN-gamma bias of released cytokines. The stimulatory effect was influenced by the length of the attached chain. In particular, the long-chained triazole analogues have a comparable stimulatory effect on cytokine production as alpha-GalCer and exhibit a stronger Th2 cytokine response.