title: Efficient synthesis of 4-amido-N(5)-acetyl-4-deoxyneuraminic acid and its application to the C-4 modification of sialic acids.
abstract: A straightforward synthesis of 4-amido-N(5)-acetyl-4-deoxyneuraminic acid, a key precursor to various 4-amidoneuraminic acid analogues, has been achieved using a highly regioselective and diastereoselective [3 + 2]-cycloaddition of d-mannose-derived nitrone with methyl acrylate. Advantages of this newly developed synthesis include the use of economically available materials and reagents, the ease of operations and the excellent control of stereochemistry, as well as the convenience in application to the C-4 modifications of sialic acids.
authors.affiliation: State Key Laboratory of Bioorganic & Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.
authors.forename: Zheng-Xi
authors.initials: ZX
authors.lastname: Gao
authors.forename: Meng
authors.initials: M
authors.lastname: Wang
authors.forename: Shaozhong
authors.initials: S
authors.lastname: Wang
authors.forename: Zhu-Jun
authors.initials: ZJ
authors.lastname: Yao
mesh_terms: D003500:Cyclization; D005942:Gluconates / Q000737:chemistry*; D015394:Molecular Structure; D019158:N-Acetylneuraminic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D012794:Sialic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C544887:4-amido-N5-acetyl-4-deoxyneuraminic acid; D005942:Gluconates; D012794:Sialic Acids; D019158:N-Acetylneuraminic Acid