Oxidation with pyridinium chlorochromate of the aminoalditols 3 and 5, obtained by reaction of a protected aldose with a primary amine and then with a Grignard reagent, affords alpha-keto-acid derivatives which undergo decarboxylation to lactams 4 and 6. Starting from 2,3,5-tri-O-benzyl-D-arabinose, lactam 4 is the only product, whereas starting from 2,3,4,6-tetra-O-benzyl-D-glucose or -mannose, alpha-keto ester 7 is the main product.
Cipolla, L., Nicotra, F., Pangrazio, C. (1996). Synthesis of azasugars. Unexpected results in the oxidative cyclization of aminoalditols. GAZZETTA CHIMICA ITALIANA, 126(10), 663-666.
Synthesis of azasugars. Unexpected results in the oxidative cyclization of aminoalditols
CIPOLLA, LAURA FRANCESCA;NICOTRA, FRANCESCO;
1996
Abstract
Oxidation with pyridinium chlorochromate of the aminoalditols 3 and 5, obtained by reaction of a protected aldose with a primary amine and then with a Grignard reagent, affords alpha-keto-acid derivatives which undergo decarboxylation to lactams 4 and 6. Starting from 2,3,5-tri-O-benzyl-D-arabinose, lactam 4 is the only product, whereas starting from 2,3,4,6-tetra-O-benzyl-D-glucose or -mannose, alpha-keto ester 7 is the main product.
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