[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-octadecylsulfanyloxan-2-yl]methyl acetate | 179032-24-7

• 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: [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-octadecylsulfanyloxan-2-yl]methyl acetate
• CAS: 179032-24-7
• 化学式: C₃₂H₅₆O₉S
• 分子量: 616.857
• InChiKey: GHWBELZKSSICBK-VJLURNNQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.2
• 重原子数：
  42
• 可旋转键数：
  27
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  140
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-octadecylsulfanyloxan-2-yl]methyl acetate 生成 (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-octadecylsulfanyloxane-3,4,5-triol
  参考文献：
  名称：

  Lauryl and Stearyl Thioglycosides: Preparation and Reactivity of the Glycosyl Donor

  摘要：

  月桂醇和硬脂醇硫糖苷是通过路易斯酸催化的反应制备的，该反应涉及1-O-乙酰化糖与非挥发性和几乎无气味的壬基硫醇和十八烷硫醇。将这些硫糖苷用N-碘琥珀酰亚胺-TfOH激活，生成优良产率的二糖供体。

  DOI：

  10.1246/cl.2000.326
• 作为产物：
  描述：

  [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-carbamimidoylsulfanyloxan-2-yl]methyl acetate;hydrobromide 、 硬脂基溴 在 potassium carbonate 、 sodium hydrogensulfite 作用下， 以 水 、 丙酮 为溶剂， 以90%的产率得到[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-octadecylsulfanyloxan-2-yl]methyl acetate
  参考文献：
  名称：

  Synthetic studies on the relationship between anti-HIV activities and micelle forming abilities of various alkylated glycyrrhetinate diglycoside sodium sulfates and related compounds

  摘要：

  Sodium sulfates 11-14, 29-32, 35 and 37 of various alkyl glycyrrhizin and related compounds were synthesized. In vitro anti-HIV activities of the sulfates were compared to the activities of glycyrrhizin 1 in the inhibition of replications of HTLV-III and GUN-4. The activities of the sulfates were increased 11.1, 15.2, 9.1 and 5.0 times for 11-14, 100.0, 125.5, 83.3 and 11.6 times for 29-32, and 11.6 and 50.0 times for 35 and 37. From the relationship between CMC values and anti-HIV activities of the sulfates, it appeared that the sulfates exhibiting more potent antiviral activities had higher micelle forming abilities. Sodium sulfates having a triterpenoid or steroid ring in the molecule showed more potent activities than those of thioglycosides which had no such ring. From the investigation of syncytium formation, we suggest that the active sulfates inhibited HIV-1 infection early in the replication cycle of the virus.

  DOI：

  10.1016/0223-5234(96)89163-x