O-(β-D-glucopyranosyl)pyridine-2-carbaldoxime | 405139-87-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: O-(β-D-glucopyranosyl)pyridine-2-carbaldoxime
• 英文别名: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[(E)-pyridin-2-ylmethylideneamino]oxyoxane-3,4,5-triol
• CAS: 405139-87-9
• 化学式: C₁₂H₁₆N₂O₆
• 分子量: 284.269
• InChiKey: LMUDZLLKGBUQMA-YBHSHDQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  125
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 O-(β-D-glucopyranosyl)pyridine-2-carbaldoxime 以 吡啶 为溶剂， 反应 16.0h， 以100%的产率得到O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)pyridine-2carbaldoxime
  参考文献：
  名称：

  Enantioselective catalysis. Part 142: Carbohydrate-derived oxime ethers from functionalised aldehydes and O-β-d-glucopyranosylhydroxylamine—new CN ligands stable towards hydrolysis

  摘要：

  A new way of linking carbohydrates to phosphorus- or nitrogen-containing aldehydes via oxime ethers is described resulting in novel C=N ligands which are stable towards hydrolysis. Reaction Of O-beta -D-glucopyranosythydroxylamine 2 with 2-diphenylphosphanylbenzaldehyde 3 or pyridine-2-carbaldehyde 4 afforded the oxime ethers O-(beta -D-glucopyranosyl)-2-diphenylphosphanylbenzaldoxime 5 and O-(beta -D-glucopyranosyl)pyridine-2-carbaldoxime 6. After peracetylation of the hydroxyl groups in 5 and 6, the protected sugar derivatives O-(2,3,4,6-tetra-O-acetyl-beta -D-glucopyranosyl)-2-diphenylphosphanylbenzaldoxime 7 and O-(2,3,4,6-tetra-O-acetyl-beta -D-glucopyranosyl)pyridine-2-carbaldoxime 8 were obtained. The molecular structure of 7 was established by X-ray diffraction studies. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00451-7
• 作为产物：
  描述：

  1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)pyrrolidine-2,5-dione 在 盐酸 、 一水合肼 作用下， 以 甲醇 、 水 为溶剂， 反应 74.0h， 生成 O-(β-D-glucopyranosyl)pyridine-2-carbaldoxime
  参考文献：
  名称：

  Enantioselective catalysis. Part 142: Carbohydrate-derived oxime ethers from functionalised aldehydes and O-β-d-glucopyranosylhydroxylamine—new CN ligands stable towards hydrolysis

  摘要：

  A new way of linking carbohydrates to phosphorus- or nitrogen-containing aldehydes via oxime ethers is described resulting in novel C=N ligands which are stable towards hydrolysis. Reaction Of O-beta -D-glucopyranosythydroxylamine 2 with 2-diphenylphosphanylbenzaldehyde 3 or pyridine-2-carbaldehyde 4 afforded the oxime ethers O-(beta -D-glucopyranosyl)-2-diphenylphosphanylbenzaldoxime 5 and O-(beta -D-glucopyranosyl)pyridine-2-carbaldoxime 6. After peracetylation of the hydroxyl groups in 5 and 6, the protected sugar derivatives O-(2,3,4,6-tetra-O-acetyl-beta -D-glucopyranosyl)-2-diphenylphosphanylbenzaldoxime 7 and O-(2,3,4,6-tetra-O-acetyl-beta -D-glucopyranosyl)pyridine-2-carbaldoxime 8 were obtained. The molecular structure of 7 was established by X-ray diffraction studies. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00451-7

文献信息

• Enantioselective catalysis. Part 142: Carbohydrate-derived oxime ethers from functionalised aldehydes and O-β-d-glucopyranosylhydroxylamine—new CN ligands stable towards hydrolysis
  作者：Henri Brunner、Maximilian Schönherr、Manfred Zabel

  DOI：10.1016/s0957-4166(01)00451-7

  日期：2001.10

  A new way of linking carbohydrates to phosphorus- or nitrogen-containing aldehydes via oxime ethers is described resulting in novel C=N ligands which are stable towards hydrolysis. Reaction Of O-beta -D-glucopyranosythydroxylamine 2 with 2-diphenylphosphanylbenzaldehyde 3 or pyridine-2-carbaldehyde 4 afforded the oxime ethers O-(beta -D-glucopyranosyl)-2-diphenylphosphanylbenzaldoxime 5 and O-(beta -D-glucopyranosyl)pyridine-2-carbaldoxime 6. After peracetylation of the hydroxyl groups in 5 and 6, the protected sugar derivatives O-(2,3,4,6-tetra-O-acetyl-beta -D-glucopyranosyl)-2-diphenylphosphanylbenzaldoxime 7 and O-(2,3,4,6-tetra-O-acetyl-beta -D-glucopyranosyl)pyridine-2-carbaldoxime 8 were obtained. The molecular structure of 7 was established by X-ray diffraction studies. (C) 2001 Elsevier Science Ltd. All rights reserved.