N-(2-amino-2-deoxy-β-D-glucopyranosyl)-N-octadecyldodecanamide | 113484-14-3

• 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-amino-2-deoxy-β-D-glucopyranosyl)-N-octadecyldodecanamide
• 英文别名: N-(2-amino-2-deoxy-β-D-glucopyranosyl)-N-octadecyl-dodecanoamide；N-[(2R,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-N-octadecyldodecanamide
• CAS: 113484-14-3
• 化学式: C₃₆H₇₂N₂O₅
• 分子量: 612.978
• InChiKey: KVOQTUQRZIJBMN-PIKNNPIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.3
• 重原子数：
  43
• 可旋转键数：
  29
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(2-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 19.0h， 生成 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：

  ethyl dodecanoyl carbonate 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 19.0h， 生成 N-(2-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

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.