(2R,3S,4R,5R,6S)-2-((2S,3S,4R)-2-Azido-3,4-bis-benzyloxy-octadecyloxy)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran | 848827-40-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4R,5R,6S)-2-((2S,3S,4R)-2-Azido-3,4-bis-benzyloxy-octadecyloxy)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran
• CAS: 848827-40-7
• 化学式: C₅₉H₇₇N₃O₇
• 分子量: 940.276
• InChiKey: PYOKTYDKPNUIKI-IFCPWDBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.44
• 重原子数：
  69.0
• 可旋转键数：
  34.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  113.37
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R,5R,6S)-2-((2S,3S,4R)-2-Azido-3,4-bis-benzyloxy-octadecyloxy)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran 在 吡啶 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 三苯基膦 作用下， 以 水 、 1,2-二氯乙烷 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of α-galactosyl ceramide and the related glycolipids for evaluation of their activities on mouse splenocytes

  摘要：

  Phytosphingosine and its short-chain analog were efficiently synthesized with 19% overall yield in 10 steps, respectively, starting from an inexpensive D-lyxose. Galactosyl donors of sulfide and phosphite types bearing benzoyl protecting groups of 4- and 6OH underwent glycosylation in excellent alpha-anomeric selectivity. A variety of alpha-galactosyl, fucosyl and glucosyl ceramides and serine-type lipids were prepared, and their activities involved in the proliferation of mouse splenocytes and the expression of cytokines were elucidated. Besides alpha-galactosyl ceramides, a galactosyl serine-type lipid also exhibited substantial effect on the expression of cytokines IFN-gamma and IL-4. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.12.027
• 作为产物：
  描述：

  3,4-O-isopropylidene-1-O-triphenylmethyl-D-arabino-octadec-5-en-1,2,3,4-tetraol 在 palladium dihydroxide 、 4 A molecular sieve 吡啶 、 2,6-二甲基吡啶 、 2-氯吡啶 、 二甲基硫 、 三氟甲磺酸酐 、 4 A molecular sieve 、 氢气 、 sodium hydride 、 溶剂黄146 、 tetramethylguanidinum azide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 (2R,3S,4R,5R,6S)-2-((2S,3S,4R)-2-Azido-3,4-bis-benzyloxy-octadecyloxy)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran
  参考文献：
  名称：

  Synthesis of α-galactosyl ceramide and the related glycolipids for evaluation of their activities on mouse splenocytes

  摘要：

  Phytosphingosine and its short-chain analog were efficiently synthesized with 19% overall yield in 10 steps, respectively, starting from an inexpensive D-lyxose. Galactosyl donors of sulfide and phosphite types bearing benzoyl protecting groups of 4- and 6OH underwent glycosylation in excellent alpha-anomeric selectivity. A variety of alpha-galactosyl, fucosyl and glucosyl ceramides and serine-type lipids were prepared, and their activities involved in the proliferation of mouse splenocytes and the expression of cytokines were elucidated. Besides alpha-galactosyl ceramides, a galactosyl serine-type lipid also exhibited substantial effect on the expression of cytokines IFN-gamma and IL-4. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.12.027

文献信息

• Synthesis and biological activity of α-l-fucosyl ceramides, analogues of the potent agonist, α-d-galactosyl ceramide KRN7000
  作者：Natacha Veerapen、Faye Reddington、Gabriel Bricard、Steven A. Porcelli、Gurdyal S. Besra

  DOI：10.1016/j.bmcl.2010.04.079

  日期：2010.6

  these conditions. α-Galactosyl ceramide (α-GalCer) is a known agonist of iNKT cells and it is believed that its fucosyl counterpart might have similar immunogenic properties. We herein report the synthesis of α-l-fucosyl ceramide derivatives and describe their biological evaluation. The key challenge in the synthesis of the target molecules involved the stereoselective synthesis of the α-glycosidic

  几种l-岩藻糖脂与癌症、囊性纤维化和类风湿性关节炎等疾病有关。激活我NKT细胞是已知的导致细胞因子的产生，可帮助缓解或加剧这些条件。α半乳糖基神经酰胺（α-神经酰胺）是一个已知激动剂我NKT细胞，并且据信其岩藻糖基对应物可能具有相似的免疫原性。我们在此报告了α- l的合成-岩藻糖神经酰胺衍生物并描述其生物学评价。目标分子合成中的关键挑战涉及α-糖苷键的立体选择性合成。在检查的方法中，per-TMS 保护的糖基碘供体是完全α-选择性的，并且可以按比例放大以提供克数量的叠氮化物前体11，其中一系列 N-酰化 α- l-岩藻糖基神经酰胺是容易获得并评估人i NKT 细胞的体外扩增。