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Triacetonide of Glucoheptonic Acid in the Scalable Syntheses of d-Gulose, 6-Deoxy-d-gulose, l-Glucose, 6-Deoxy-l-glucose, and Related Sugars. 2016

Zilei Liu, and Akihide Yoshihara, and Sarah F Jenkinson, and Mark R Wormald, and Ramón J Estévez, and George W J Fleet, and Ken Izumori
Chemistry Research Laboratory, Department of Chemistry, University of Oxford , Oxford OX1 3TA, U.K.

Ease of separation of petrol-soluble acetonides derived from the triacetonide of methyl glucoheptonate allows scalable syntheses of rare sugars containing the l-gluco or d-gulo structural motif with any oxidation level at the C6 or C1 position of the hexose, usually without chromatography: meso-d-glycero-d-guloheptitol available in two steps is an ideal entry point for the study of the biotechnological production of heptoses.

UI MeSH Term Description Entries
D008968 Molecular Conformation The characteristic three-dimensional shape of a molecule. Molecular Configuration,3D Molecular Structure,Configuration, Molecular,Molecular Structure, Three Dimensional,Three Dimensional Molecular Structure,3D Molecular Structures,Configurations, Molecular,Conformation, Molecular,Conformations, Molecular,Molecular Configurations,Molecular Conformations,Molecular Structure, 3D,Molecular Structures, 3D,Structure, 3D Molecular,Structures, 3D Molecular
D006601 Hexoses MONOSACCHARIDES whose molecules contain six carbon atoms, such as GLUCOSE and FRUCTOSE. They generally have the chemical formula C6H12O6. Hexose
D000073893 Sugars Short chain carbohydrate molecules that have hydroxyl groups attached to each carbon atom unit with the exception of one carbon that has a doubly-bond aldehyde or ketone oxygen. Cyclical sugar molecules are formed when the aldehyde or ketone groups respectively form a hemiacetal or hemiketal bond with one of the hydroxyl carbons. The three dimensional structure of the sugar molecule occurs in a vast array of biological and synthetic classes of specialized compounds including AMINO SUGARS; CARBASUGARS; DEOXY SUGARS; SUGAR ACIDS; SUGAR ALCOHOLS; and SUGAR PHOSPHATES. Sugar
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D013400 Sugar Acids MONOSACCHARIDES and other sugars that contain one or more carboxylic acid moieties. Acids, Sugar

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