N-(2-(N-benzyloxycarbonyl-L-phenylalanyl)amino-2-deoxy-β-D-glucopyranosyl)-N-dodecyloctadecanamide | 113484-50-7

• 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: N-(2-(N-benzyloxycarbonyl-L-phenylalanyl)amino-2-deoxy-β-D-glucopyranosyl)-N-dodecyloctadecanamide
• 英文别名: N-(2-(N-benzyloxycarbonyl-L-phenylalaninamido)-2-deoxy-β-D-glucopyranosyl)-N-dodecyl-octadecanoamide；benzyl N-[(2S)-1-[[(2R,3R,4R,5S,6R)-2-[dodecyl(octadecanoyl)amino]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]amino]-1-oxo-3-phenylpropan-2-yl]carbamate
• CAS: 113484-50-7
• 化学式: C₅₃H₈₇N₃O₈
• 分子量: 894.289
• InChiKey: LLKRCILAPLHYDU-ZRTYGHDTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.8
• 重原子数：
  64
• 可旋转键数：
  37
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  158
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-(2-(N-benzyloxycarbonyl-L-phenylalanyl)amino-2-deoxy-β-D-glucopyranosyl)-N-dodecyloctadecanamide 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83.5%的产率得到N-(2-deoxy-2-L-phenylalanylamino-β-D-glucopyranosyl)-N-dodecyloctadecanamide
  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：

  carbethoxy oleate 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-L-phenylalanyl)amino-2-deoxy-β-D-glucopyranosyl)-N-dodecyloctadecanamide
  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

文献信息

• N-(2-Aminoacylamido-2-desoxy-hexosyl)-amide, -carbamate und -harnstoffe, Verfahren zu ihrer Herstellung sowie ihre Verwendung in Arzneimitteln
  申请人：BAYER AG

  公开号：EP0206037B1

  公开（公告）日：1992-01-15
• US4855283A
  申请人：——

  公开号：US4855283A

  公开（公告）日：1989-08-08
• Syntheses of Peptidoglycolipid Analogs with Distinct Immunomodulating Activities
  作者：Oswald Lockhoff、Yutaka Hayauchi

  DOI：10.1080/07328300008544102

  日期：2000.1

  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.