title: Benzylidene Acetal Protecting Group as Carboxylic Acid Surrogate: Synthesis of Functionalized Uronic Acids and Sugar Amino Acids.
abstract: Direct oxidation of the 4,6-O-benzylidene acetal protecting group to C-6 carboxylic acid has been developed that provides an easy access to a wide range of biologically important and synthetically challenging uronic acid and sugar amino acid derivatives in good yields. The RuCl3 -NaIO4 -mediated oxidative cleavage method eliminates protection and deprotection steps and the reaction takes place under mild conditions. The dual role of the benzylidene acetal, as a protecting group and source of carboxylic acid, was exploited in the efficient synthesis of six-carbon sialic acid analogues and disaccharides bearing uronic acids, including glycosaminoglycan analogues.
authors.affiliation: Department of Chemistry, Indian Institute of Technology Madras, Chennai-, 600036, India.
authors.forename: Amit
authors.initials: A
authors.lastname: Banerjee
authors.affiliation: Department of Chemistry, Indian Institute of Technology Madras, Chennai-, 600036, India.
authors.forename: Soundararasu
authors.initials: S
authors.lastname: Senthilkumar
authors.affiliation: Department of Chemistry, Indian Institute of Technology Madras, Chennai-, 600036, India. sbhaskar@iitm.ac.in.
authors.forename: Sundarababu
authors.initials: S
authors.lastname: Baskaran
mesh_terms: D000080:Acetals / Q000737:chemistry*; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D000606:Amino Sugars / Q000138:chemical synthesis* / Q000737:chemistry; D001597:Benzylidene Compounds / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D006025:Glycosaminoglycans / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D014574:Uronic Acids / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000080:Acetals; D000596:Amino Acids; D000606:Amino Sugars; D001597:Benzylidene Compounds; D002264:Carboxylic Acids; D006025:Glycosaminoglycans; D014574:Uronic Acids
keywords: acetals; amino acids; carboxylic acids; oxidation; protecting groups; uronic acids