(2S,3S,4R)-2-azido-3,4-di-O-para-methoxybenzyl-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-octadecane | 853055-34-2

• 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: (2S,3S,4R)-2-azido-3,4-di-O-para-methoxybenzyl-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-octadecane
• 英文别名: (2S,3R,4S,5S,6R)-2-[(2S,3S,4R)-2-azido-3,4-bis[(4-methoxyphenyl)methoxy]octadecoxy]-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 853055-34-2
• 化学式: C₆₈H₈₇N₃O₁₀
• 分子量: 1106.45
• InChiKey: KVFPPURZRCJROK-BXLGKZHKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.4
• 重原子数：
  81
• 可旋转键数：
  40
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  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 在 吡啶 、 4-二甲氨基吡啶 、 sodium sulfide 、 硫酸 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 19.0h， 生成 (2S,3S,4R)-3,4-di-O-para-methoxybenzyl-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2-(N-octacosylamino)-4-octadecane
  参考文献：
  名称：

  Efficient Synthesis of α-Galactosyl Ceramide Analogues Using Glycosyl Iodide Donors

  摘要：

  The combination of reactive galactosyl iodide donors with electron-rich acceptor lipids provides highly stereoselective and efficient routes to a GalCer analogues. Using per-O-silylated donors, key intermediates can be obtained in a three-step, one-pot sequence providing useful constructs for analogue development.

  DOI：

  10.1021/ol050659f
• 作为产物：
  描述：

  糖脂 在 吡啶 、 甲醇 、 4 A molecular sieve 、 triflic azide 、 三氟化硼乙醚 、 四丁基碘化铵 、 sodium hydride 、 potassium carbonate 、 copper(II) sulfate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 苯 为溶剂， 反应 29.5h， 生成 (2S,3S,4R)-2-azido-3,4-di-O-para-methoxybenzyl-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-octadecane
  参考文献：
  名称：

  Efficient Synthesis of α-Galactosyl Ceramide Analogues Using Glycosyl Iodide Donors

  摘要：

  The combination of reactive galactosyl iodide donors with electron-rich acceptor lipids provides highly stereoselective and efficient routes to a GalCer analogues. Using per-O-silylated donors, key intermediates can be obtained in a three-step, one-pot sequence providing useful constructs for analogue development.

  DOI：

  10.1021/ol050659f

文献信息

• ALPHA-GALACTOSYLCERAMIDE DERIVATIVES, PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF, PREPARATION METHOD AND PHARMACEUTICAL COMPOSITION FOR THE IMMUNE ADJUVANT CONTAINING THE SAME AS AN ACTIVE INGREDIENT
  申请人：Kang Chang-Yuil

  公开号：US20100104590A1

  公开（公告）日：2010-04-29

  Disclosed are novel α-galactosylceramide derivatives, pharmaceutically acceptable salts thereof, preparation methods thereof, and pharmaceutical compositions for use in an immune adjuvant containing the same as an active ingredient. The derivatives, in which the amide moiety of α-GalCer is bioisosterically replaced with a triazole moiety, direct cytokine secretion toward IL-4 rather than IFN-γ and thus can be used as a therapeutic for autoimmune diseases regulated by IL-4, such as type 1 diabetes and multiple sclerosis.

  揭示了新颖的α-半乳糖鞘氨醇衍生物，其药用可接受的盐，其制备方法以及用于免疫佐剂的药物组合物，其中包含其作为活性成分。这些衍生物中，α-半乳糖鞘氨醇的酰胺基团被三唑基团生物异构地替代，将细胞因子分泌定向于IL-4而非IFN-γ，因此可以用作治疗由IL-4调节的自身免疫疾病，如1型糖尿病和多发性硬化症。
• WO2008/82156
  申请人：——

  公开号：——

  公开（公告）日：——
• 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.
• Efficient Synthesis of α-Galactosyl Ceramide Analogues Using Glycosyl Iodide Donors
  作者：Wenjun Du、Jacquelyn Gervay-Hague

  DOI：10.1021/ol050659f

  日期：2005.5.1

  The combination of reactive galactosyl iodide donors with electron-rich acceptor lipids provides highly stereoselective and efficient routes to a GalCer analogues. Using per-O-silylated donors, key intermediates can be obtained in a three-step, one-pot sequence providing useful constructs for analogue development.