1,2,3,5,6-penta-O-acetyl-L-idofuranose | 328379-60-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,2,3,5,6-penta-O-acetyl-L-idofuranose
• 英文别名: L-idofuranosyl pentaacetate
• CAS: 328379-60-8
• 化学式: C₁₆H₂₂O₁₁
• 分子量: 390.344
• InChiKey: JRZQXPYZEBBLPJ-JPIQDLEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.37
• 重原子数：
  27.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  140.73
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  1,2,3,5,6-penta-O-acetyl-L-idofuranose 在 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 3.0h， 生成 (4-nitro)phenyl β-L-idofuranoside
  参考文献：
  名称：

  Non-natural aldofuranosides as substrates of a β-glucosidase

  摘要：

  Based on glycosidase inhibitory activities of some known 1,4-iminoalditols, four aldofuranosides, (4-nitro)phenyl beta-D-glucofuranoside, -beta-D-galactofuranoside, -alpha-L-idofuranoside and -alpha-L-altrofuranoside, were identified as possible substrates of glucosidases and galactosidases. Three of them were found to be accepted by the beta-glucosidase from Agrobacterium sp. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.027
• 作为产物：
  描述：

  乙酸酐 、 3,5,6-tri-O-acetyl-1,2-O-isopropylidene-β-L-idofuranose 在 硫酸 、 溶剂黄146 作用下， 生成 1,2,3,5,6-penta-O-acetyl-L-idofuranose
  参考文献：
  名称：

  Non-natural aldofuranosides as substrates of a β-glucosidase

  摘要：

  Based on glycosidase inhibitory activities of some known 1,4-iminoalditols, four aldofuranosides, (4-nitro)phenyl beta-D-glucofuranoside, -beta-D-galactofuranoside, -alpha-L-idofuranoside and -alpha-L-altrofuranoside, were identified as possible substrates of glucosidases and galactosidases. Three of them were found to be accepted by the beta-glucosidase from Agrobacterium sp. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.027

文献信息

• Efficient Synthesis of 1,2,3,4,6-Penta-<i>O</i>-acetyl-<scp>L</scp>-idopyranose
  作者：Shang-Cheng Hung、Chien-Sheng Chen

  DOI：10.1002/jccs.200000173

  日期：2000.12

  An efficient synthesis of 1,2,3,4,6-penta-O-acetyl-L-idopyranose 2 from 3,5-O-benzylidene-1,2-O-isopropylidene-α-D-glucofuranose in five steps in 45% overall yield via hydroboration of enol ether, hydrolysis of L-idofuranosyl sugar and acetolysis of 1,6-anhydro-β-L-idopyranose as key steps is described here.

  由 3,5-O-亚苄基-1,2-O-异亚丙基-α-D-呋喃葡萄糖通过五个步骤高效合成 1,2,3,4,6-五-O-乙酰基-L-吡喃糖 2此处描述了通过烯醇醚的硼氢化、L-idofuranosyl 糖的水解和 1,6-脱水-β-L-idopyranose 的乙酰化作为关键步骤的 45% 总产率。
• 1,6-Anhydro-β- l -hexopyranoses as valuable building blocks toward the synthesis of l -gulosamine and l -altrose derivatives
  作者：Shang-Cheng Hung、Cheng-Chung Wang、Shu-Wen Chang、Chien-Sheng Chen

  DOI：10.1016/s0040-4039(00)02237-1

  日期：2001.2

  1,6-Anhydro-beta -L-hexopyranoses as valuable building blocks toward the synthesis of L-gulosamine and L-altrose derivatives via the regioselective triflation and benzoylation of 1,6-anhydro-beta -L-idopyranose followed by S(N)2 substitution with various nucleophiles as key steps is described here. (C) 2001 Elsevier Science Ltd. All rights reserved.