(4E)-1S-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-2,4,5-trideoxy-2-octadecanoylamino-1-thio-6-O-undecyl-D-erythro-hex-4-enitol | 1172607-66-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4E)-1S-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-2,4,5-trideoxy-2-octadecanoylamino-1-thio-6-O-undecyl-D-erythro-hex-4-enitol
• CAS: 1172607-66-7
• 化学式: C₄₉H₈₈N₂O₁₁S
• 分子量: 913.311
• InChiKey: DOWGFNCHZPPYTF-KAEUNUHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.59
• 重原子数：
  63.0
• 可旋转键数：
  39.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  175.79
• 氢给体数：
  3.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  (4E)-1S-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-2,4,5-trideoxy-2-octadecanoylamino-1-thio-6-O-undecyl-D-erythro-hex-4-enitol 在 氨 作用下， 以 甲醇 为溶剂， 反应 4.5h， 以96%的产率得到(4E)-1S-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-2,4,5-trideoxy-2-octadecanoylamino-1-thio-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：

  三氟甲磺酸酐 、 (4E)-1S-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-2,4,5-trideoxy-3-O-methoxymethyl-2-octadecanoylamino-1-thio-6-O-undecyl-D-erythro-hex-4-enitol 以 乙腈 为溶剂， 反应 2.0h， 以87%的产率得到(4E)-1S-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-2,4,5-trideoxy-2-octadecanoylamino-1-thio-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