(2S,3S,4R)-1-O-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)-2-(8''-phenyloctylamino)-1,3,4-octadecanetriol | 1448529-91-6

• 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-(8''-phenyloctylamino)-1,3,4-octadecanetriol
• 英文别名: (2S,3S,4R)-1-O-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)-2-(8"-phenyloctylamino)-1,3,4-octadecanetriol
• CAS: 1448529-91-6
• 化学式: C₆₆H₉₃NO₈
• 分子量: 1028.47
• InChiKey: QLFGIUKUIKHXOX-FGWKQXODSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.06
• 重原子数：
  75.0
• 可旋转键数：
  41.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  107.87
• 氢给体数：
  3.0
• 氢受体数：
  9.0

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-(8''-phenyloctylamino)-1,3,4-octadecanetriol 在 20% palladium hydroxide-activated charcoal 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 以78%的产率得到(2S,3S,4R)-1-O-(α-D-galactopyranosyl)-2-(8"-phenyloctylamino)-1,3,4-octadecanetriol
  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
• 作为产物：
  描述：

  (2S,3S,4R)-2-叠氮基-1,3,4-三-O-[(叔-丁基二甲基硅烷基)氧基]十八烷 在 sodium tetrahydroborate 、 N-碘代丁二酰亚胺 、 nickel(II) chloride hexahydrate 、 三氟甲磺酸 、 四丁基氟化铵 、 sodium cyanoborohydride 、 溶剂黄146 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 5.5h， 生成 (2S,3S,4R)-1-O-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)-2-(8''-phenyloctylamino)-1,3,4-octadecanetriol
  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