heptyl 2-(acetylamino)-2-deoxy-α-D-glucopyranoside | 225791-95-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: heptyl 2-(acetylamino)-2-deoxy-α-D-glucopyranoside
• 英文别名: heptyl 2-acetamido-2-deoxy-α-D-glucopyranoside；N-[(2S,3R,4R,5S,6R)-2-heptoxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 225791-95-7
• 化学式: C₁₅H₂₉NO₆
• 分子量: 319.398
• InChiKey: SRZQFVHBXUJPDN-RYPNDVFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  108
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  heptyl 2-(acetylamino)-2-deoxy-α-D-glucopyranoside 在 sodium hydride 、 对甲苯磺酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 生成 heptyl 2-(acetylamino)-2-deoxy-4,6-O-isopropylidene-3-O-[(R)-1-carboxyethyl]-α-D-glucopyranoside
  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：

  [(2R,3S,4R,5R,6S)-5-acetamido-3,4-diacetyloxy-6-heptoxyoxan-2-yl]methyl acetate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以87%的产率得到heptyl 2-(acetylamino)-2-deoxy-α-D-glucopyranoside
  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

文献信息

• Zemlyakov; Kur'yanov; Tsikalov, Russian Journal of Bioorganic Chemistry, 1998, vol. 24, # 6, p. 393 - 397
  作者：Zemlyakov、Kur'yanov、Tsikalov、Chirva

  DOI：——

  日期：——