{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Hinton H"],"funding":["National Science Foundation"],"pagination":["5087"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC10343380"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["28(13)"],"pubmed_abstract":["This paper describes the three-step synthesis of TBS-MAC, a masked acyl cyanide (MAC) and a versatile one-carbon oxidation state three synthon. We have developed a scalable and detailed synthesis that involves: (1) acetylation of malononitrile to form the sodium enolate, (2) protonation of the enolate to form acetylmalononitrile, and (3) epoxidation of the enol, rearrangement to an unstable alcohol, and TBS-protection to form the title compound. Both the sodium enolate and acetylmalononitrile are bench-stable precursors to the intermediate hydroxymalononitrile, which can be converted to other MAC reagents beyond TBS by varying the protecting group (Ac, MOM, EE, etc.)."],"journal":["Molecules (Basel, Switzerland)"],"pubmed_title":["Scalable Preparation of the Masked Acyl Cyanide TBS-MAC."],"pmcid":["PMC10343380"],"funding_grant_id":["1848257"],"pubmed_authors":["Hinton H","Patterson J","Pigza J","Hume J","Patel K"],"additional_accession":[]},"is_claimable":false,"name":"Scalable Preparation of the Masked Acyl Cyanide TBS-MAC.","description":"This paper describes the three-step synthesis of TBS-MAC, a masked acyl cyanide (MAC) and a versatile one-carbon oxidation state three synthon. We have developed a scalable and detailed synthesis that involves: (1) acetylation of malononitrile to form the sodium enolate, (2) protonation of the enolate to form acetylmalononitrile, and (3) epoxidation of the enol, rearrangement to an unstable alcohol, and TBS-protection to form the title compound. Both the sodium enolate and acetylmalononitrile are bench-stable precursors to the intermediate hydroxymalononitrile, which can be converted to other MAC reagents beyond TBS by varying the protecting group (Ac, MOM, EE, etc.).","dates":{"release":"2023-01-01T00:00:00Z","publication":"2023 Jun","modification":"2025-04-19T04:59:53.484Z","creation":"2025-04-19T04:59:53.484Z"},"accession":"S-EPMC10343380","cross_references":{"pubmed":["37446749"],"doi":["10.3390/molecules28135087"]}}