2'-azidoethyl 3,6-di-O-pivaloyl-α-D-glucopyranoside | 1374977-06-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2'-azidoethyl 3,6-di-O-pivaloyl-α-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-6-(2-azidoethoxy)-4-(2,2-dimethylpropanoyloxy)-3,5-dihydroxyoxan-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 1374977-06-6
• 化学式: C₁₈H₃₁N₃O₈
• 分子量: 417.459
• InChiKey: MMAAXDNSDWORMN-XGFWRYKXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  126
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2'-azidoethyl 3,6-di-O-pivaloyl-α-D-glucopyranoside 在 5%-palladium/activated carbon 、 三氟化硼乙醚 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 54.0h， 生成 2'-aminoethyl 2,4-di-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-3,6-di-O-pivaloyl-α-D-glucopyranoside
  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：

  三甲基乙酰氯 、 (2R,3R,4S,5S,6R)-2-(2-Azido-ethoxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 在 吡啶 作用下， 以1.73 g的产率得到2'-azidoethyl 3,6-di-O-pivaloyl-α-D-glucopyranoside
  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

文献信息

• Multicomponent Synthesis of Ugi-Type Ceramide Analogues and Neoglycolipids from Lipidic Isocyanides
  作者：Karell Pérez-Labrada、Ignacio Brouard、Inmaculada Méndez、Daniel G. Rivera

  DOI：10.1021/jo300462m

  日期：2012.5.18

  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.