Acetic acid (2S,3R,4R,5S,6S)-4,5-diacetoxy-6-methyl-2-[(2R,6S)-6-(2-methyl-cyclohex-2-enyl)-3-oxo-3,6-dihydro-2H-pyran-2-ylmethoxy]-tetrahydro-pyran-3-yl ester | 188198-95-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: Acetic acid (2S,3R,4R,5S,6S)-4,5-diacetoxy-6-methyl-2-[(2R,6S)-6-(2-methyl-cyclohex-2-enyl)-3-oxo-3,6-dihydro-2H-pyran-2-ylmethoxy]-tetrahydro-pyran-3-yl ester
• CAS: 188198-95-0
• 化学式: C₂₅H₃₄O₁₀
• 分子量: 494.539
• InChiKey: BQPYPBODNWKKMT-GNYKIYHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.18
• 重原子数：
  35.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  123.66
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2S,3R,4R,5S,6S)-4,5-diacetoxy-6-methyl-2-[(2R,6S)-6-(2-methyl-cyclohex-2-enyl)-3-oxo-3,6-dihydro-2H-pyran-2-ylmethoxy]-tetrahydro-pyran-3-yl ester 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以43%的产率得到(2R,6S)-6-(2-Methyl-cyclohex-2-enyl)-2-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxymethyl)-6H-pyran-3-one
  参考文献：
  名称：

  Hexose keto-C-glycoside conjugates: design, synthesis, cytotoxicity, and evaluation of their affinity for the glucose transporter glut-1

  摘要：

  The design, synthesis, cytotoxicity, and biological evaluation of carbohydrate/C-glycoside conjugates are described. The design concept is predicted on the idea that physiological barriers like the blood brain barrier could be crossed selectively by using glucose or glucose derivative/drug conjugates. The study demonstrates that, (I) carbohydrates and C-glycosides can be bonded at nonanomeric positions by the reaction of carbohydrate triflates with C-glycoside alkoxydes in the presence of DMPU; (2) there is a structure-activity relationship between the cytotoxicity of the conjugate and the nature of the carbohydrate residue; and (3) peracetylated hexose keto-C-glycoside conjugates are the most cytotoxic keto-C-glycosides. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0968-0896(96)00224-6
• 作为产物：
  描述：

  Acetic acid (2S,3R,4R,5S,6S)-4,5-diacetoxy-2-[(2R,3S,6S)-3-hydroxy-6-(2-methyl-cyclohex-2-enyl)-3,6-dihydro-2H-pyran-2-ylmethoxy]-6-methyl-tetrahydro-pyran-3-yl ester 在 重铬酸吡啶 、 4 Angstroem MS 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以67%的产率得到Acetic acid (2S,3R,4R,5S,6S)-4,5-diacetoxy-6-methyl-2-[(2R,6S)-6-(2-methyl-cyclohex-2-enyl)-3-oxo-3,6-dihydro-2H-pyran-2-ylmethoxy]-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Hexose keto-C-glycoside conjugates: design, synthesis, cytotoxicity, and evaluation of their affinity for the glucose transporter glut-1

  摘要：

  The design, synthesis, cytotoxicity, and biological evaluation of carbohydrate/C-glycoside conjugates are described. The design concept is predicted on the idea that physiological barriers like the blood brain barrier could be crossed selectively by using glucose or glucose derivative/drug conjugates. The study demonstrates that, (I) carbohydrates and C-glycosides can be bonded at nonanomeric positions by the reaction of carbohydrate triflates with C-glycoside alkoxydes in the presence of DMPU; (2) there is a structure-activity relationship between the cytotoxicity of the conjugate and the nature of the carbohydrate residue; and (3) peracetylated hexose keto-C-glycoside conjugates are the most cytotoxic keto-C-glycosides. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0968-0896(96)00224-6