Trifluoro-methanesulfonic acid (2R,3S,6S)-3-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-6-(2-methyl-cyclohex-2-enyl)-3,6-dihydro-2H-pyran-2-ylmethyl ester | 188199-02-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: Trifluoro-methanesulfonic acid (2R,3S,6S)-3-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-6-(2-methyl-cyclohex-2-enyl)-3,6-dihydro-2H-pyran-2-ylmethyl ester
• CAS: 188199-02-2
• 化学式: C₂₂H₃₇F₃O₅SSi
• 分子量: 498.679
• InChiKey: OBADYFHLSSIJLX-SEBOWIOWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.95
• 重原子数：
  32.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Trifluoro-methanesulfonic acid (2R,3S,6S)-3-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-6-(2-methyl-cyclohex-2-enyl)-3,6-dihydro-2H-pyran-2-ylmethyl ester 在 N,N-二甲基丙烯基脲 、 重铬酸吡啶 、 4 Angstroem MS 、 sodium hydride 、 tetra(tert-butyl)-ammonium fluoride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.83h， 生成 (2R,6S)-6-(2-Methyl-cyclohex-2-enyl)-2-((3aR,3bS,7R,7aR,8aR)-2,2,5,5-tetramethyl-tetrahydro-[1,3]dioxolo[4,5]furo[3,2-d][1,3]dioxin-7-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 、 甲酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 Trifluoro-methanesulfonic acid (2R,3S,6S)-3-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-6-(2-methyl-cyclohex-2-enyl)-3,6-dihydro-2H-pyran-2-ylmethyl 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