(2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-(4-hydroxyphenethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate | 1283670-85-8

• 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,3S,4S,5R,6R)-2-(acetoxymethyl)-6-(4-hydroxyphenethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• CAS: 1283670-85-8
• 化学式: C₂₂H₂₈O₁₁
• 分子量: 468.458
• InChiKey: UZIWUYYGCYEJFF-CDJZJNNCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.03
• 重原子数：
  33.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  143.89
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-(4-hydroxyphenethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 在 甲醇 、 sodium methylate 作用下， 反应 24.0h， 以3.6 kg的产率得到2-(4-hydroxyphenyl)ethyl β-D-galactopyranoside
  参考文献：
  名称：

  Development of a Kilogram-Scale Synthesis of Salidroside and Its Analogs

  摘要：

  An efficient, safe, and viable process has been developed for large-scale preparation of salidroside, a natural product. The process consists of two chemical steps, which produce the salidroside on a multikilogram scale with 72% overall yield and >98% purity. A series of novel salidroside analogs were prepared according to the same method.

  DOI：

  10.1080/00397911.2010.515332
• 作为产物：
  描述：

  2-(4-甲基羰基氧基苯基)-1-乙醇 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃糖溴化物 在 silver carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 16.67h， 生成 (2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-(4-hydroxyphenethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
  参考文献：
  名称：

  Development of a Kilogram-Scale Synthesis of Salidroside and Its Analogs

  摘要：

  An efficient, safe, and viable process has been developed for large-scale preparation of salidroside, a natural product. The process consists of two chemical steps, which produce the salidroside on a multikilogram scale with 72% overall yield and >98% purity. A series of novel salidroside analogs were prepared according to the same method.

  DOI：

  10.1080/00397911.2010.515332