hexyl 2-(acetylamino)-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside | 500767-92-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: hexyl 2-(acetylamino)-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside
• 英文别名: N-[(4aR,6R,7R,8R,8aS)-6-hexoxy-8-hydroxy-2,2-dimethyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]acetamide
• CAS: 500767-92-0
• 化学式: C₁₇H₃₁NO₆
• 分子量: 345.436
• InChiKey: QOMOEAOHFDQHIK-OXGONZEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.33
• 重原子数：
  24.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  86.25
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  hexyl 2-(acetylamino)-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside 在 sodium hydride 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 生成 (R)-4-{(S)-2-[(R)-2-((4aR,6R,7R,8R,8aS)-7-Acetylamino-6-hexyloxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-propionylamino]-propionylamino}-4-carbamoyl-butyric acid benzyl ester
  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：

  己基-2,3,4,6-四-氧-乙酰基-β-D-吡喃葡萄糖苷 在 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 hexyl 2-(acetylamino)-2-deoxy-4,6-O-isopropylidene-β-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