(4E)-2-azido-2,4,5-trideoxy-3-O-methoxymethyl-6-O-undecyl-D-erythro-hex-4-enitol | 1172607-63-4

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (4E)-2-azido-2,4,5-trideoxy-3-O-methoxymethyl-6-O-undecyl-D-erythro-hex-4-enitol
• CAS: 1172607-63-4
• 化学式: C₁₉H₃₇N₃O₄
• 分子量: 371.52
• InChiKey: DWHARQAVILBHFP-UBJZUDALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.75
• 重原子数：
  26.0
• 可旋转键数：
  19.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  96.68
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  三氟甲磺酸酐 、 (4E)-2-azido-2,4,5-trideoxy-3-O-methoxymethyl-6-O-undecyl-D-erythro-hex-4-enitol 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 (4E)-2-azido-2,4,5-trideoxy-3-O-methoxymethyl-1-O-[(trifluoromethyl)sulfonyl]-6-O-undecyl-D-erythro-hex-4-enitol
  参考文献：
  名称：

  合成和评价ñ -乙酰基-2-氨基-2-脱氧α -D-半乳糖基-1-硫代-7- oxaceramide，一种新的模拟α -D-半乳糖基神经酰胺

  摘要：

  Abstractmagnified imageThe N‐acetyl‐2‐amino‐2‐deoxy‐α‐D‐galactopyranosyl 1‐thio‐7‐oxaceramide 1 was synthesized by substituting the 7‐oxasphingosine triflate 3 with α‐D‐N‐acetyl‐1‐thiogalactosamine (2). The triflate 3 was obtained from azide 4. Thiol 2 was prepared according to a known procedure from α‐D‐galactosamine hydrochloride. As compared to ceramide (Cer), 1 is neither a substrate of ceramide kinase (CerK), consistent with the absence of the C(1)OH group, nor an inhibitor of Cer phosphorylation by CerK. While 1 partially displaced CD1d‐bound lipids, it failed to stimulate invariant natural killer T (iNKT) cells when presented by human CD1d‐transfected cells. These results suggest that 1 binds weakly to recombinant CD1d, but does not form immunogenic complexes with CD1d.

  DOI：

  10.1002/hlca.200800454
• 作为产物：
  描述：

  (4E)-2-azido-1-O-[(tert-butyl)diphenylsilyl]-2,4,5-trideoxy-3-O-methoxymethyl-6-O-undecyl-D-erythro-hex-4-enitol 在 溶剂黄146 、 tetra-n-butylammoniumfluoride trihydrate 作用下， 以 四氢呋喃 为溶剂， 以95%的产率得到(4E)-2-azido-2,4,5-trideoxy-3-O-methoxymethyl-6-O-undecyl-D-erythro-hex-4-enitol
  参考文献：
  名称：

  合成和评价ñ -乙酰基-2-氨基-2-脱氧α -D-半乳糖基-1-硫代-7- oxaceramide，一种新的模拟α -D-半乳糖基神经酰胺

  摘要：

  Abstractmagnified imageThe N‐acetyl‐2‐amino‐2‐deoxy‐α‐D‐galactopyranosyl 1‐thio‐7‐oxaceramide 1 was synthesized by substituting the 7‐oxasphingosine triflate 3 with α‐D‐N‐acetyl‐1‐thiogalactosamine (2). The triflate 3 was obtained from azide 4. Thiol 2 was prepared according to a known procedure from α‐D‐galactosamine hydrochloride. As compared to ceramide (Cer), 1 is neither a substrate of ceramide kinase (CerK), consistent with the absence of the C(1)OH group, nor an inhibitor of Cer phosphorylation by CerK. While 1 partially displaced CD1d‐bound lipids, it failed to stimulate invariant natural killer T (iNKT) cells when presented by human CD1d‐transfected cells. These results suggest that 1 binds weakly to recombinant CD1d, but does not form immunogenic complexes with CD1d.

  DOI：

  10.1002/hlca.200800454