1,2-isopropylidene-5-O-(2-methoxyethyl)-3-O-methyl-6-O-trityl-α-D-glucofuranose | 172744-72-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1,2-isopropylidene-5-O-(2-methoxyethyl)-3-O-methyl-6-O-trityl-α-D-glucofuranose
• CAS: 172744-72-8
• 化学式: C₃₂H₃₈O₇
• 分子量: 534.65
• InChiKey: ASRSANDYRMPWHL-CMPUJJQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.92
• 重原子数：
  39.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  64.61
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1,2-isopropylidene-5-O-(2-methoxyethyl)-3-O-methyl-6-O-trityl-α-D-glucofuranose 在 4-甲基苯磺酸吡啶 作用下， 以 甲醇 为溶剂， 反应 0.17h， 生成
  参考文献：
  名称：

  Enhanced reactivity of secondary hydroxyl groups in the O-alkylation of carbohydrate-related primary-secondaryvic-glycols. Regioselective 2-O-benzylation of 1,3:2,4-di-O-ethylidene-D-glucitol

  摘要：

  Partial O-alkylation of 1,3:2,4-di-O-ethylidene-D-glucitol (1a), 1,2-O-isopropylidene-3-O-methyl-alpha-D-glucofuranose (1b), and R-(+)-1-O-benzylglycerol (1c) with benzyl chloride in a KOH/DMSO system results in products of monoalkylation at the secondary (4a-c) and at the primary hydroxyl (2a-c) in ratios of over 95:5 (a), -2:1 (b), and -1:1 (c), whereas (+/-)propane-1,2-diol (1d) gives only the product of 1-O-benzylation (2d). A qualitatively similar result is observed upon O-alkylation of diols (la-e) with 2-methoxyethanol tosylate.

  DOI：

  10.1007/bf00704019
• 作为产物：
  描述：

  1,2-O-isopropylidene-3-O-methyl-α-D-glucofuranose 在 氢氧化钾 作用下， 以 吡啶 、 二甲基亚砜 为溶剂， 反应 8.0h， 生成 1,2-isopropylidene-5-O-(2-methoxyethyl)-3-O-methyl-6-O-trityl-α-D-glucofuranose
  参考文献：
  名称：

  Enhanced reactivity of secondary hydroxyl groups in the O-alkylation of carbohydrate-related primary-secondaryvic-glycols. Regioselective 2-O-benzylation of 1,3:2,4-di-O-ethylidene-D-glucitol

  摘要：

  Partial O-alkylation of 1,3:2,4-di-O-ethylidene-D-glucitol (1a), 1,2-O-isopropylidene-3-O-methyl-alpha-D-glucofuranose (1b), and R-(+)-1-O-benzylglycerol (1c) with benzyl chloride in a KOH/DMSO system results in products of monoalkylation at the secondary (4a-c) and at the primary hydroxyl (2a-c) in ratios of over 95:5 (a), -2:1 (b), and -1:1 (c), whereas (+/-)propane-1,2-diol (1d) gives only the product of 1-O-benzylation (2d). A qualitatively similar result is observed upon O-alkylation of diols (la-e) with 2-methoxyethanol tosylate.

  DOI：

  10.1007/bf00704019