[(2R,3R,4S,5R,6R)-4-(2,2-dimethylpropanoyloxy)-6-[2-[dodecyl-[2-(octadecylamino)-2-oxoethyl]amino]-2-oxoethoxy]-3,5-bis[[(2S,3R,4R,5S,6S)-3,4,5-triacetyloxy-6-methyloxan-2-yl]oxy]oxan-2-yl]methyl 2,2-dimethylpropanoate | 1374977-20-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [(2R,3R,4S,5R,6R)-4-(2,2-dimethylpropanoyloxy)-6-[2-[dodecyl-[2-(octadecylamino)-2-oxoethyl]amino]-2-oxoethoxy]-3,5-bis[[(2S,3R,4R,5S,6S)-3,4,5-triacetyloxy-6-methyloxan-2-yl]oxy]oxan-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 1374977-20-4
• 化学式: C₇₄H₁₂₆N₂O₂₄
• 分子量: 1427.81
• InChiKey: DHOMAUSABPBTIY-FYJQVGHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.9
• 重原子数：
  100
• 可旋转键数：
  56
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  315
• 氢给体数：
  1
• 氢受体数：
  24

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4S,5R,6R)-4-(2,2-dimethylpropanoyloxy)-6-[2-[dodecyl-[2-(octadecylamino)-2-oxoethyl]amino]-2-oxoethoxy]-3,5-bis[[(2S,3R,4R,5S,6S)-3,4,5-triacetyloxy-6-methyloxan-2-yl]oxy]oxan-2-yl]methyl 2,2-dimethylpropanoate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以96%的产率得到2-[dodecyl-[2-[(2R,3R,4S,5S,6R)-4-hydroxy-6-(hydroxymethyl)-3,5-bis[[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy]oxan-2-yl]oxyacetyl]amino]-N-octadecylacetamide
  参考文献：
  名称：

  Multicomponent Synthesis of Ugi-Type Ceramide Analogues and Neoglycolipids from Lipidic Isocyanides

  摘要：

  Unique types of ceramide and glycolipid architectures were obtained by means of Ugi reactions incorporating lipidic isocyanides as surrogates of sphingolipids. The multicomponent nature of this approach allowed for a highly efficient assembly process, wherein two of the components provided the lipidic tails while a third one incorporated either the functionality suitable for the conjugation to sugar or the sugar moiety itself. Two dissimilar strategies were implemented: (i) the initial assembly of ceramide analogues followed by glycosylation to produce a glycolipid skeleton and (ii) the one-pot construction of glycolipid frameworks by condensation of lipidic isocyanides either with lipidic amines and oligosaccharidic acids or with fatty acids and oligosaccharidic amines. Whereas both approaches are amenable for accessing analogues of anticancer glycolipids, the latter one proved to have greater potential owing to its more straightforward and efficient character. Overall, the methodology developed shows great promise toward the massive (eventually combinatorial) production of neoglycolipids suitable for biological screening.

  DOI：

  10.1021/jo300462m
• 作为产物：
  描述：

  聚合甲醛 、 十二烷基伯胺 、 carboxymethyl 2,4-di-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-3,6-di-O-pivaloyl-α-D-glucopyranoside 、 1-isocyanooctadecane 以 甲醇 、 二氯甲烷 、 四氢呋喃 为溶剂， 反应 1.0h， 以72%的产率得到[(2R,3R,4S,5R,6R)-4-(2,2-dimethylpropanoyloxy)-6-[2-[dodecyl-[2-(octadecylamino)-2-oxoethyl]amino]-2-oxoethoxy]-3,5-bis[[(2S,3R,4R,5S,6S)-3,4,5-triacetyloxy-6-methyloxan-2-yl]oxy]oxan-2-yl]methyl 2,2-dimethylpropanoate
  参考文献：
  名称：

  Multicomponent Synthesis of Ugi-Type Ceramide Analogues and Neoglycolipids from Lipidic Isocyanides

  摘要：

  Unique types of ceramide and glycolipid architectures were obtained by means of Ugi reactions incorporating lipidic isocyanides as surrogates of sphingolipids. The multicomponent nature of this approach allowed for a highly efficient assembly process, wherein two of the components provided the lipidic tails while a third one incorporated either the functionality suitable for the conjugation to sugar or the sugar moiety itself. Two dissimilar strategies were implemented: (i) the initial assembly of ceramide analogues followed by glycosylation to produce a glycolipid skeleton and (ii) the one-pot construction of glycolipid frameworks by condensation of lipidic isocyanides either with lipidic amines and oligosaccharidic acids or with fatty acids and oligosaccharidic amines. Whereas both approaches are amenable for accessing analogues of anticancer glycolipids, the latter one proved to have greater potential owing to its more straightforward and efficient character. Overall, the methodology developed shows great promise toward the massive (eventually combinatorial) production of neoglycolipids suitable for biological screening.

  DOI：

  10.1021/jo300462m