Synthesis of Novel Pyran β-Amino Acid and 5,6-Dihydro-2H-pyran β-aminoxy Acid from Carbohydrate Derivatives

Author： Sridhar Gattu   Hanumaiah Marumamula   Sharma Gangavaram V. M.  

Publisher： Taylor & Francis Ltd

E-ISSN： 1532-2432|45|15|1768-1776

ISSN： 0039-7911

Source： Synthetic Communications, Vol.45, Iss.15, 2015-08, pp. : 1768-1776

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Abstract

Synthesis of two new amino acids, containing pyran rings, is reported from carbohydrate derivatives. The cis-3-amino-pyran-2-carboxylic acid (cis-APyC) was prepared from (R)-glyceraldehyde derivative, using nucleophilic substitution reaction for pyran ring formation. Similarly, the trans-3-aminoxy-5,6-dihydro-2H-pyran-2-carboxylic acid (trans-AmPyC) was prepared from diacetone glucose (DAG), using ring closing metathesis (RCM) reaction for the ring formation.

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