((S)-1-{(2R,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-[((Z)-octadec-9-enoyl)-octadecyl-amino]-tetrahydro-pyran-3-ylcarbamoyl}-2-hydroxy-ethyl)-carbamic acid tert-butyl ester | 294664-87-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ((S)-1-{(2R,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-[((Z)-octadec-9-enoyl)-octadecyl-amino]-tetrahydro-pyran-3-ylcarbamoyl}-2-hydroxy-ethyl)-carbamic acid tert-butyl ester
• CAS: 294664-87-2
• 化学式: C₅₀H₉₅N₃O₉
• 分子量: 882.319
• InChiKey: CECGBNICEBVHCY-VWUSSWSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.92
• 重原子数：
  62.0
• 可旋转键数：
  38.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  177.89
• 氢给体数：
  6.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  ((S)-1-{(2R,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-[((Z)-octadec-9-enoyl)-octadecyl-amino]-tetrahydro-pyran-3-ylcarbamoyl}-2-hydroxy-ethyl)-carbamic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以87.1%的产率得到(Z)-N-(2-deoxy-2-L-serylamino-β-D-glucopyranosyl)-N-octadecyl-9-octadecenamide
  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 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 34.0h， 生成 ((S)-1-{(2R,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-[((Z)-octadec-9-enoyl)-octadecyl-amino]-tetrahydro-pyran-3-ylcarbamoyl}-2-hydroxy-ethyl)-carbamic acid tert-butyl ester
  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