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

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• 作者：Tomasz Gubica ; 艁ukasz Szeleszczuk ; Dariusz M. Pisklak ; Dorota K. St臋pie艅 ; Micha艂 K. Cyra艅ski ; Marianna Ka艅ska
• 关键词：Carbohydrates ; Organic nitrates ; Conformational analysis ; X-ray diffraction ; Solid-state NMR ; DFT optimization
• 刊名：Tetrahedron
• 出版年：11 March, 2014
• 年：2014
• 卷：70
• 期：10
• 页码：1910-1917
• 全文大小：722 K

文摘

In this paper the comparative structural analysis of a series of compounds (methyl 伪-d-glucopyranoside, methyl 4,6-O-ethylidene-伪-d-glucopyranoside (g class="boldFont">2g>), methyl 2,3-di-O-nitro-4,6-O-ethylidene-伪-d-glucopyranoside聽and methyl 3-O-nitro-4,6-O-ethylidene-伪-d-glucopyranoside) by way of synthesis leading to methyl 3-O-nitro-伪-d-glucopyranoside (g class="boldFont">5g>) is reported. The title compound (g class="boldFont">5g>) 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), ¹³C CP/MAS NMR spectroscopy and DFT calculations. In the case of g class="boldFont">2g> and g class="boldFont">5g>, XRD analysis could not be performed due to the fact that g class="boldFont">2g> is highly hygroscopic and g class="boldFont">5g> forms improper crystals. However, the molecular structures of g class="boldFont">2g> and g class="boldFont">5g> 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 ¹³C CP/MAS NMR spectral data.