A novel approach to the synthesis of amino-sugars. Routes to selectively protected 3-amino-3-deoxy-aldopentoses based on pyridinium salt photochemistry.
A new approach for the synthesis of selectively blocked 3-amino-3-deoxyaldopentoses is presented. The strategy is based on employment of a pyridinium salt photocyclization-aziridine ring-opening sequence to prepare stereochemically defined, enantiomerically enriched aminocyclopentendiol derivatives. Ring-opening reactions transform these substances into terminally differentiated aminopolyols, which serve as precursors to the target amino-aldopentoses. The utility of this strategy is demonstrated by its application to the syntheses of protected derivatives of D- and L-3-amino-3-deoxyxylose, L-3-amino-3-deoxyarabinose, and a late-stage intermediate in a potential route to N-acetylneuraminic acid.
Lu
Haiyan
H
Department of Chemistry, University of New Mexico, Albuquerque, New Mexico 87131, USA.
Su
Zhuoyi
Z
Song
Ling
L
Mariano
Patrick S
PS
D000606:Amino Sugars / Q000138:chemical synthesis*; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D003500:Cyclization; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010777:Photochemistry; D011726:Pyridinium Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D000606:Amino Sugars; D011726:Pyridinium Compounds