Studies for the transformation of carbocycles into carbohydrates: approach toward the synthesis of higher sugar derivatives.
A highly stereocontrolled synthesis of a beta-D-ribo-hept-6-ulopyranosuronamide derivative, a useful intermediate for the synthesis of other higher sugars, has been developed using naturally occurring (-)-quinic acid as a chiral starting material. The transformation of carbocycle to carbohydrate, a key step in this sequence, occurred in a one-pot reaction: an ozonolysis carried out under mild conditions.
Baptistella
Lúcia Helena Brito
LH
Instituto de Química, UNICAMP, CP 6154, 13084-971 Campinas, SP, Brazil. lhbb@iqm.unicamp.br
Cerchiaro
Giselle
G
D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry*; D003500:Cyclization; D015394:Molecular Structure; D024301:Plant Bark / Q000737:chemistry; D011801:Quinic Acid / Q000737:chemistry; D013237:Stereoisomerism
D002241:Carbohydrates; D011801:Quinic Acid