THE ACID-CATALYZED DEHYDRATION OF (METHYL β-D-glycero-D-gulo-HEPTOPYRANOSID)URONIC ACID

Article abstract of DOI:10.1016/S0008-6215(00)80812-5

The major product soluble in organic solvents, isolated by hydrolysis and subsequent dehydration of (methyl β-D-glycero-D-gulo-heptopyranosid)uronic acid (1) in M sulfuric acid solution at 100 deg C, is 5-hydroxymethyl-2-furaldehyde (2), presumably produced via loss of C-7 by decarboxylation.The mechanism of the conversion was studied by synthesis of the <1-(14)C>1 and conversion to 5-hydroxymethyl-2-fur<(14)C>aldehyde (2-(14)C).Conversion of 1 into 2-(14)C in acidified D2O, followed by measurement of C-bound D by 1H-n.m.r.-m.s. showed that 2-(14)C was labeled only at D-3 (40 atom percent) of the furan ring.The major portion of the water-soluble materials was shown (by m.s.) to be D-glycero-D-gulo-hepturonic acid, and lactone derived therefrom, resulting from the hydrolysis of 1.