Heteroglycoclusters through Unprecedented Orthogonal Chemistry Based on N‐Alkylation of N‐Acylhydrazone. Issue 33 (1st April 2022)

• Record Type: Journal Article
• Authors: Fray, Marwa; Mathiron, David; Pilard, Serge; Lesur, David; Abidi, Rym; Barhoumi‐Slimi, Thouraya; Cragg, Peter J.; Benazza, Mohammed
• Is Part Of: European journal of organic chemistry. Volume 2022:Issue 33(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-04-01
• Subjects: Cone calix/1, 3-alt thiacalixarene -- Heteroglycoclusters -- N-acylhydrazone -- N-alkyl-N-acylhydrazone -- Orthogonal chemistry; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202101537
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: Orthogonal chemistry is a valuable tool in the preparation of complex molecules as heteroglycoclusters. Unfortunately, selective heteroconjugation of multifunctional starting materials remains a usually challenging problem to overcome. Herein, we report the first report on harnessing N ‐alkylation of N ‐acylhydrazone as a key step in the orthogonal synthesis. Sequentially associated with the azido‐alkyne click chemistry, it stands out as a new and straightforward synthetic method of glycoconjugate small molecules, heterodisaccharides, and heteroglycoclusters based on cone p ‐ t Bu‐calix[4]arene and 1, 3‐ alt p ‐ t Bu‐thiacalix[4]arene with potential drug‐like properties. Abstract : We report a new orthogonal strategy involving the N ‐alkylation of N ‐acylhydrazone as a key step. When followed by azido‐alkyne click chemistry, it represents a new and straightforward synthetic method to prepare N ‐alkyl‐NAH glycoconjugates of small molecules, heterodisaccharides, and heteroglycoclusters‐based on cone p ‐ t Bu‐calix[4]arene and 1, 3‐ alt p ‐ t Bu‐thiacalix[4]arene with potential drug‐like properties.