(2S,3S,4R)-1-O-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)-2-azido-3,4-di-tert-butyldimethylsilyloxyoctadecane | 1256376-22-3

• 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)-1-O-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)-2-azido-3,4-di-tert-butyldimethylsilyloxyoctadecane
• 英文别名: (2S,3S,4R)-2-azido-3,4-bis-tert-butyldimethylsilyloxy-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)octadecane；[(2S,3S,4R)-2-azido-3-[tert-butyl(dimethyl)silyl]oxy-1-[(2S,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoctadecan-4-yl]oxy-tert-butyl-dimethylsilane
• CAS: 1256376-22-3
• 化学式: C₆₄H₉₉N₃O₈Si₂
• 分子量: 1094.68
• InChiKey: XLCWTLRAUKJDSC-NQNLUXILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.25
• 重原子数：
  77
• 可旋转键数：
  38
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  88.2
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R)-1-O-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)-2-azido-3,4-di-tert-butyldimethylsilyloxyoctadecane 在 三甲基膦 、 水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 5.25h， 生成 (2S,3S,4R)-3,4-bis((tert-butyldimethylsilyl)oxy)-1-(((2S,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)octadecan-2-amine
  参考文献：
  名称：

  通过有机催化羟醛反应不对称合成α-d-半乳糖神经酰胺KRN7000

  摘要：

  描述了以（R）-脯氨酸催化的对映选择性醛醇缩合反应为关键步骤的抗肿瘤和免疫刺激性α- d-半乳糖基神经酰胺KRN7000的不对称合成。使用市售底物1-戊烯醛，2,2-二甲基-1,3-二恶烷-5-酮，己二十二酸，通过十三个线性步骤以优异的立体选择性（de> 98％，ee = 95％）合成标题化合物和d-半乳糖。 α-半乳糖基神经酰胺-不对称合成-羟醛反应-有机催化-脯氨酸

  DOI：

  10.1055/s-0029-1218844
• 作为产物：
  描述：

  (2R,3S,4R)-2-叠氮十八烷-1,3,4-三醇 在 2,6-二甲基吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 4.5h， 生成 (2S,3S,4R)-1-O-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)-2-azido-3,4-di-tert-butyldimethylsilyloxyoctadecane
  参考文献：
  名称：

  Design and synthesis of new KRN7000 analogues

  摘要：

  Presented by CD1d protein, KRN7000, a potent synthetic cc-galactosylceramide, is known to stimulate the iNKT cells to produce different bioactive cytokines. Six new KRN7000 analogues, in which the amide bond in KRN7000 is replaced with O, NH, or ester groups incorporating variation of the acyl chain, or possessing an additional four-atom linker between the galactose and phytosphingosine moiety, were designed and synthesized. The synthetic compounds were evaluated for their ability to stimulate cytokine release and the preliminary structure activity relationships were discussed. The synthetic strategy will benefit the construction of more KRN7000 derivatives, which may contribute to cytokine profile bias. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.06.051

文献信息

• Asymmetric Synthesis of the α-d-Galactosyl Ceramide KRN7000 via an Organocatalytic Aldol Reaction as Key Step
  作者：Dieter Enders、Violeta Terteryan、Jiří Paleček

  DOI：10.1055/s-0029-1218844

  日期：2010.9

  The asymmetric synthesis of the antitumor and immunostimulatory α-d-galactosyl ceramide KRN7000 using a (R)-proline-catalyzed enantioselective aldol reaction as key step is described. The title compound is synthesized in thirteen linear steps with excellent stereoselectivity (de >98%, ee = 95%) employing the commercially available substrates 1-pentadecanal, 2,2-dimethyl-1,3-dioxan-5-one, hexacosanoic

  描述了以（R）-脯氨酸催化的对映选择性醛醇缩合反应为关键步骤的抗肿瘤和免疫刺激性α- d-半乳糖基神经酰胺KRN7000的不对称合成。使用市售底物1-戊烯醛，2,2-二甲基-1,3-二恶烷-5-酮，己二十二酸，通过十三个线性步骤以优异的立体选择性（de> 98％，ee = 95％）合成标题化合物和d-半乳糖。 α-半乳糖基神经酰胺-不对称合成-羟醛反应-有机催化-脯氨酸
• Design and synthesis of new KRN7000 analogues
  作者：Man Sun、Yuhang Wang、Xin-Shan Ye

  DOI：10.1016/j.tet.2013.06.051

  日期：2013.9

  Presented by CD1d protein, KRN7000, a potent synthetic cc-galactosylceramide, is known to stimulate the iNKT cells to produce different bioactive cytokines. Six new KRN7000 analogues, in which the amide bond in KRN7000 is replaced with O, NH, or ester groups incorporating variation of the acyl chain, or possessing an additional four-atom linker between the galactose and phytosphingosine moiety, were designed and synthesized. The synthetic compounds were evaluated for their ability to stimulate cytokine release and the preliminary structure activity relationships were discussed. The synthetic strategy will benefit the construction of more KRN7000 derivatives, which may contribute to cytokine profile bias. (C) 2013 Elsevier Ltd. All rights reserved.