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来自α-保护的2-氨基-2-脱氧-D-吡喃葡萄糖的双功能叠氮（硫代）脲：合成与结构分析。

Bifunctional Azido(thio)ureas from an -Protected 2-Amino-2-deoxy-d-glucopyranose: Synthesis and Structural Analyses.

作者信息

Sosa-Gil Concepción, Matamoros Esther, Cintas Pedro, Palacios Juan C

机构信息

Departamento de Química Orgánica e Inorgánica, Facultad de Ciencias, and Instituto del Agua, Cambio Climático y Sostenibilidad (IACYS)-Unidad de Química Verde y Desarrollo Sostenible, Universidad de Extremadura, 06006 Badajoz, Spain.

Departamento de Química Orgánica, Universidad de Málaga, Campus Teatinos s/n, 29071 Málaga, Spain.

出版信息

Molecules. 2024 Nov 30;29(23):5687. doi: 10.3390/molecules29235687.

DOI:10.3390/molecules29235687
PMID:39683846
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11643871/
Abstract

This publication reports a facile and convenient preparation of tri--acetyl-glucopyranoses, derived from the corresponding 2-deoxyaminosugar, where the vicinal anomeric and C2 positions are decorated by azido and (thio)ureido groups, respectively. This double functionalization leads to an inherently chiral core incorporating the versatile azido and (thio)ureido linkages prone to further manipulation. The latter also provides a structural element for hydrogen-bonded donor-acceptor (HB-DA) sites, which are of immense value in organocatalytic pursuits. A computation-aided conformational analysis unveils the landscape of available conformers and their relative stability. -aryl (thio)ureas bearing substituents at ortho positions exist as mixtures of - and -atropisomeric conformers.

摘要

本出版物报道了一种简便易行的制备三乙酰吡喃葡萄糖的方法，该方法由相应的2-脱氧氨基糖衍生而来，其中邻位异头碳和C2位分别被叠氮基和（硫）脲基修饰。这种双重功能化导致了一个固有的手性核心，该核心包含易于进一步操作的多功能叠氮基和（硫）脲键。后者还为氢键供体-受体（HB-DA）位点提供了一个结构元素，这在有机催化研究中具有巨大价值。计算机辅助构象分析揭示了可用构象体的情况及其相对稳定性。在邻位带有取代基的芳基（硫）脲以 - 和 - 阻转异构构象体的混合物形式存在。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f6b0/11643871/1e9efdbf7f55/molecules-29-05687-sch008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f6b0/11643871/d61ff3c41074/molecules-29-05687-ch001.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f6b0/11643871/0e8d3b1e5ce4/molecules-29-05687-sch004.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f6b0/11643871/4bfc6079e591/molecules-29-05687-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f6b0/11643871/5246b707fc8f/molecules-29-05687-sch006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f6b0/11643871/f3f7b6f18cc4/molecules-29-05687-g003.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f6b0/11643871/9f148ed1b04c/molecules-29-05687-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f6b0/11643871/06d2ff92700e/molecules-29-05687-ch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f6b0/11643871/323c01d9cf7d/molecules-29-05687-sch007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f6b0/11643871/e1072cd046dc/molecules-29-05687-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f6b0/11643871/b4282061090e/molecules-29-05687-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f6b0/11643871/1e9efdbf7f55/molecules-29-05687-sch008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f6b0/11643871/d61ff3c41074/molecules-29-05687-ch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f6b0/11643871/22ab0053643f/molecules-29-05687-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f6b0/11643871/1b6135452a3c/molecules-29-05687-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f6b0/11643871/58ecdf49bfe9/molecules-29-05687-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f6b0/11643871/532242bb773c/molecules-29-05687-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f6b0/11643871/0e8d3b1e5ce4/molecules-29-05687-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f6b0/11643871/c2d078590f40/molecules-29-05687-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f6b0/11643871/4bfc6079e591/molecules-29-05687-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f6b0/11643871/5246b707fc8f/molecules-29-05687-sch006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f6b0/11643871/f3f7b6f18cc4/molecules-29-05687-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f6b0/11643871/a2fe050a91ed/molecules-29-05687-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f6b0/11643871/3c7303e6f98f/molecules-29-05687-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f6b0/11643871/9f148ed1b04c/molecules-29-05687-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f6b0/11643871/06d2ff92700e/molecules-29-05687-ch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f6b0/11643871/323c01d9cf7d/molecules-29-05687-sch007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f6b0/11643871/e1072cd046dc/molecules-29-05687-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f6b0/11643871/b4282061090e/molecules-29-05687-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f6b0/11643871/1e9efdbf7f55/molecules-29-05687-sch008.jpg

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