benzyl (4R)-4-[[(2S)-2-[[(2R)-2-[(2R,3R,4R,5S,6R)-3-acetamido-2-hexoxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxypropanoyl]amino]propanoyl]amino]-5-amino-5-oxopentanoate | 500767-94-2

• 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: benzyl (4R)-4-[[(2S)-2-[[(2R)-2-[(2R,3R,4R,5S,6R)-3-acetamido-2-hexoxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxypropanoyl]amino]propanoyl]amino]-5-amino-5-oxopentanoate
• CAS: 500767-94-2
• 化学式: C₃₂H₅₀N₄O₁₁
• 分子量: 666.769
• InChiKey: AODVRMHICJCPIA-ZCWOMSLTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.06
• 重原子数：
  47.0
• 可旋转键数：
  20.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  224.84
• 氢给体数：
  6.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  benzyl (4R)-4-[[(2S)-2-[[(2R)-2-[(2R,3R,4R,5S,6R)-3-acetamido-2-hexoxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxypropanoyl]amino]propanoyl]amino]-5-amino-5-oxopentanoate 在 10% palladium on active carbon 氢气 作用下， 以 乙醇 为溶剂， 以78%的产率得到(4R)-4-[[(2S)-2-[[(2R)-2-[(2R,3R,4R,5S,6R)-3-acetamido-2-hexoxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxypropanoyl]amino]propanoyl]amino]-5-amino-5-oxopentanoic acid
  参考文献：
  名称：

  摘要：

  Hexyl, octyl, and cyclohexyl beta-glycosides and heptyl and cyclohexyl alpha-glycosides of muramyl dipeptide (MDP) were synthesized. Tests in vitro and in vivo revealed lower immunostimulating activities of MDP alpha-glycosides in comparison with the corresponding beta-glycosides and MDP itself. In the case of alkyl beta-glycosides, differences in hydrocarbon chain lengths (C-4-C-8) and in aglycone (aliphatic chain and aliphatic or aromatic ring) exerted no substantial effect on the immunostimulating activity.

  DOI：

  10.1023/a:1023944818406
• 作为产物：
  描述：

  hexyl 2-(acetylamino)-2-deoxy-4,6-O-isopropylidene-3-O-[(R)-1-carboxyethyl]-β-D-glucopyranoside 在 溶剂黄146 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 水 为溶剂， 生成 benzyl (4R)-4-[[(2S)-2-[[(2R)-2-[(2R,3R,4R,5S,6R)-3-acetamido-2-hexoxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxypropanoyl]amino]propanoyl]amino]-5-amino-5-oxopentanoate
  参考文献：
  名称：

  摘要：

  Hexyl, octyl, and cyclohexyl beta-glycosides and heptyl and cyclohexyl alpha-glycosides of muramyl dipeptide (MDP) were synthesized. Tests in vitro and in vivo revealed lower immunostimulating activities of MDP alpha-glycosides in comparison with the corresponding beta-glycosides and MDP itself. In the case of alkyl beta-glycosides, differences in hydrocarbon chain lengths (C-4-C-8) and in aglycone (aliphatic chain and aliphatic or aromatic ring) exerted no substantial effect on the immunostimulating activity.

  DOI：

  10.1023/a:1023944818406