methyl 3-O-nitro-4,6-O-ethylidene-α-D-glucopyranoside | 18634-76-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: methyl 3-O-nitro-4,6-O-ethylidene-α-D-glucopyranoside
• 英文别名: Methyl-4,6-O-ethyliden-α-D-glucopyranosid-3-nitrat；4,6-O-Aethyliden-3-O-nitro-α-methylglucosid；4,6-O-Aethyliden-α-methyl-D-glucosid-nitrat-(3)
• CAS: 18634-76-9
• 化学式: C₉H₁₅NO₈
• 分子量: 265.22
• InChiKey: UMYBEDPKKLVMRQ-KTTWVITLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.94
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  109.52
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  methyl 3-O-nitro-4,6-O-ethylidene-α-D-glucopyranoside 在 硫酸 、 sodium methylate 作用下， 以 乙酸酐 、 甲醇 、 氯仿 为溶剂， 反应 0.41h， 以45%的产率得到methyl 3-O-nitro-α-D-glucopyranoside
  参考文献：
  名称：

  Reliable evaluation of molecular structure of methyl 3-O-nitro-α-d-glucopyranoside and its intermediates by means of solid-state NMR spectroscopy and DFT optimization in the absence of appropriate crystallographic data

  摘要：

  In this paper the comparative structural analysis of a series of compounds (methyl alpha-D-glucopyranoside, methyl 4,6-O-ethylidene-alpha-D-glucopyranoside (2), methyl 2,3-di-O-nitro-4,6-O-ethylidene-a-oglucopyranoside and methyl 3-O-nitro-4,6-O-ethylidene-u-o-glucopyranoside) by way of synthesis leading to methyl 3-O-nitro-alpha-D-glucopyranoside (5) is reported. The title compound (5) is a novel D-glucosidic mononitrate having potential biological activity against cardiovascular diseases. The structural analysis was supported by single-crystal X-ray diffraction (XRD),C-13 CP/MAS NMR spectroscopy and DFT calculations. In the case of 2 and 5, XRD analysis could not be performed due to the fact that 2 is highly hygroscopic and 5 forms improper crystals. However, the molecular structures of 2 and 5 were obtained on the basis of experimental (existing XRD data for similar compounds) and theoretical (DFT optimization) approaches. This showed of very good agreement with the C-13 CP/MAS NMR spectral data. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.01.027
• 作为产物：
  描述：

  methyl 2,3-di-O-nitro-4,6-O-ethylidene-α-D-glucopyranoside 在 sodium nitrite 作用下， 以 乙醇 、 水 为溶剂， 反应 21.0h， 以52%的产率得到methyl 3-O-nitro-4,6-O-ethylidene-α-D-glucopyranoside
  参考文献：
  名称：

  Reliable evaluation of molecular structure of methyl 3-O-nitro-α-d-glucopyranoside and its intermediates by means of solid-state NMR spectroscopy and DFT optimization in the absence of appropriate crystallographic data

  摘要：

  In this paper the comparative structural analysis of a series of compounds (methyl alpha-D-glucopyranoside, methyl 4,6-O-ethylidene-alpha-D-glucopyranoside (2), methyl 2,3-di-O-nitro-4,6-O-ethylidene-a-oglucopyranoside and methyl 3-O-nitro-4,6-O-ethylidene-u-o-glucopyranoside) by way of synthesis leading to methyl 3-O-nitro-alpha-D-glucopyranoside (5) is reported. The title compound (5) is a novel D-glucosidic mononitrate having potential biological activity against cardiovascular diseases. The structural analysis was supported by single-crystal X-ray diffraction (XRD),C-13 CP/MAS NMR spectroscopy and DFT calculations. In the case of 2 and 5, XRD analysis could not be performed due to the fact that 2 is highly hygroscopic and 5 forms improper crystals. However, the molecular structures of 2 and 5 were obtained on the basis of experimental (existing XRD data for similar compounds) and theoretical (DFT optimization) approaches. This showed of very good agreement with the C-13 CP/MAS NMR spectral data. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.01.027