2-trifluoromethylsulfonyloxyethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside | 1351946-65-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-trifluoromethylsulfonyloxyethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[2-(trifluoromethylsulfonyloxy)ethoxy]oxan-2-yl]methyl acetate
• CAS: 1351946-65-0
• 化学式: C₁₇H₂₃F₃O₁₃S
• 分子量: 524.423
• InChiKey: URADTHUBGIRRLG-IBEHDNSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  34
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  175
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  2-乙基-2-唑啉 、 甲基丙烯酸 、 2-trifluoromethylsulfonyloxyethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 0.23h， 生成 、 、
  参考文献：
  名称：

  A Sugar Decorated Macromolecular Bottle Brush by Carbohydrate-Initiated Cationic Ring-Opening Polymerization

  摘要：

  The capability of a range of protected glucose- (Glc), galactose- (Gal), and fructose- (Fm) based tosylates and triflates to initiate the living cationic ring-opening polymerization of 2-ethy1-2-oxazoline (EtOx) was investigated by detailed kinetic studies utilizing H-1 and F-19 NMR spectroscopy and SEC as well as MALDI and ESI TOF mass spectrometry. The Glc and Gal tosylates and a sterically hindered Fm triflate revealed slow and incomplete initiation, whereas the Glc and Gal triflates resulted in living polymerizations. Well-defined Glc as well as Gal alpha-end-functionalized PEtOx was obtained after deprotection. Functionalization of the living oxazolinium chain ends with methacrylate anions resulted in a macromonomer that was applied for RAFT polymerization. Deprotection resulted in a comb polymer that is selectively functionalized with Glc at the ends of all side chains (DPbackbone = 13, DPside (chains) = 10, PDI = 1.11).

  DOI：

  10.1021/ma202401x
• 作为产物：
  描述：

  三氟甲磺酸酐 、 1-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyloxy)-2-hydroxyethane 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以63%的产率得到2-trifluoromethylsulfonyloxyethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  A Sugar Decorated Macromolecular Bottle Brush by Carbohydrate-Initiated Cationic Ring-Opening Polymerization

  摘要：

  The capability of a range of protected glucose- (Glc), galactose- (Gal), and fructose- (Fm) based tosylates and triflates to initiate the living cationic ring-opening polymerization of 2-ethy1-2-oxazoline (EtOx) was investigated by detailed kinetic studies utilizing H-1 and F-19 NMR spectroscopy and SEC as well as MALDI and ESI TOF mass spectrometry. The Glc and Gal tosylates and a sterically hindered Fm triflate revealed slow and incomplete initiation, whereas the Glc and Gal triflates resulted in living polymerizations. Well-defined Glc as well as Gal alpha-end-functionalized PEtOx was obtained after deprotection. Functionalization of the living oxazolinium chain ends with methacrylate anions resulted in a macromonomer that was applied for RAFT polymerization. Deprotection resulted in a comb polymer that is selectively functionalized with Glc at the ends of all side chains (DPbackbone = 13, DPside (chains) = 10, PDI = 1.11).

  DOI：

  10.1021/ma202401x