Synthesis of Oligomers Derived from Amide-Linked Neuraminic Acid Analogues

• Published in: Journal of organic chemistry Vol. 69; no. 4; pp. 1001 - 1009
• Main Authors: Gregar, Travis Q, Gervay-Hague, Jacquelyn
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 20.02.2004; Amer Chemical Soc
• Subjects: Amides - chemistry; Carbohydrate Conformation; Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides; Carbohydrates. Nucleosides and nucleotides; Chemistry; Chemistry, Organic; Exact sciences and technology; Magnetic Resonance Spectroscopy; Molecular Structure; Neuraminic Acids - chemistry; Oligosaccharides - chemical synthesis; Oligosaccharides - chemistry; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; PEPTIDOMIMETICS; NMR; PEPTIDES; SOLID-PHASE SYNTHESIS; METHYL; SUGAR AMINO-ACID; N-ACETYLNEURAMINIC ACID; ACETYL; CONFORMATIONS; Anomer; Aminoacid; Analog; Carboxamide; Glycoside; Solid phase; Monomer; Oligomer; Chemical synthesis; Hydrogenation; Protection
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo035312+

N-Fluoren-9-ylmethoxycarbonyl-protected sugar amino acids derived from α-O-methoxy- and 2,3-dehydroneuraminic acids have been prepared. Incorporation of these monomer units into solid-phase synthesis led to the efficient synthesis of two series of oligomers varying from one to eight units in length. The (1→5)-linked amides of 2,3-dehydroneuraminic acid were further subjected to hydrogenation giving a third series of oligomers with a β-hydrido substituent at the anomeric carbon.