N-(2-(N-benzyloxycarbonyl-D-leucyl)amino-2-deoxy-β-D-glucopyranosyl)-N-octadecyldodecanamide | 294664-79-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-(2-(N-benzyloxycarbonyl-D-leucyl)amino-2-deoxy-β-D-glucopyranosyl)-N-octadecyldodecanamide
• 英文别名: benzyl N-[(2R)-1-[[(2R,3R,4R,5S,6R)-2-[dodecanoyl(octadecyl)amino]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate
• CAS: 294664-79-2
• 化学式: C₅₀H₈₉N₃O₈
• 分子量: 860.272
• InChiKey: XWNNPGHXBRACID-WXPCHCMDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.26
• 重原子数：
  61.0
• 可旋转键数：
  36.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  157.66
• 氢给体数：
  5.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  N-(2-(N-benzyloxycarbonyl-D-leucyl)amino-2-deoxy-β-D-glucopyranosyl)-N-octadecyldodecanamide 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.0h， 以82.5%的产率得到N-(2-deoxy-2-D-leucylamino-β-D-glucopyranosyl)-N-octadecyldodecanamide
  参考文献：
  名称：

  Syntheses of Peptidoglycolipid Analogs with Distinct Immunomodulating Activities

  摘要：

  Amphiphilic 2-amino-2-deoxy-beta-D-glucopyranosylamides were synthesized from N-protected glucosamine derivatives via N-glycosidation with fatty amines, subsequent N-acylation with fatty acid derivatives and deprotection. They could further be modified with amino acids to give peptido-glycopyranosyl amides, some of which exhibited strong immunostimulatory (BAY Q8939, 8) or immunoadjuvant (BAY R1005, 9) activities.

  DOI：

  10.1080/07328300008544102
• 作为产物：
  描述：

  十八胺 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 35.0h， 生成 N-(2-(N-benzyloxycarbonyl-D-leucyl)amino-2-deoxy-β-D-glucopyranosyl)-N-octadecyldodecanamide
  参考文献：
  名称：

  Syntheses of Peptidoglycolipid Analogs with Distinct Immunomodulating Activities

  摘要：

  Amphiphilic 2-amino-2-deoxy-beta-D-glucopyranosylamides were synthesized from N-protected glucosamine derivatives via N-glycosidation with fatty amines, subsequent N-acylation with fatty acid derivatives and deprotection. They could further be modified with amino acids to give peptido-glycopyranosyl amides, some of which exhibited strong immunostimulatory (BAY Q8939, 8) or immunoadjuvant (BAY R1005, 9) activities.

  DOI：

  10.1080/07328300008544102