(2R,6S)-6-(2-Methyl-cyclohex-2-enyl)-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxymethyl)-6H-pyran-3-one | 188199-08-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡喃类
• 英文名称: (2R,6S)-6-(2-Methyl-cyclohex-2-enyl)-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxymethyl)-6H-pyran-3-one
• CAS: 188199-08-8
• 化学式: C₂₅H₃₆O₈
• 分子量: 464.556
• InChiKey: LSACAPWJLXUZKS-ZLQUCISRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  33.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  81.68
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (2R,6S)-6-(2-Methyl-cyclohex-2-enyl)-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxymethyl)-6H-pyran-3-one 在 盐酸 作用下， 以 甲醇 为溶剂， 以40%的产率得到(2R,6S)-6-(2-Methyl-cyclohex-2-enyl)-2-((2R,3R,4S,5R)-3,4,5,6-tetrahydroxy-tetrahydro-pyran-2-ylmethoxymethyl)-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：

  Dimethyl-[(2R,3S,6S)-6-(2-methyl-cyclohex-2-enyl)-2-trityloxymethyl-3,6-dihydro-2H-pyran-3-yloxy]-(1,1,2-trimethyl-propyl)-silane 在 吡啶 、 N,N-二甲基丙烯基脲 、 重铬酸吡啶 、 甲酸 、 4 Angstroem MS 、 sodium hydride 、 tetra(tert-butyl)-ammonium fluoride 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 9.5h， 生成 (2R,6S)-6-(2-Methyl-cyclohex-2-enyl)-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxymethyl)-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