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1.
Org Biomol Chem ; 11(40): 6886-99, 2013 Sep 25.
Article in English | MEDLINE | ID: mdl-23963282

ABSTRACT

Crystal structures were obtained for the two C2 epimeric azido-γ-lactones 2-azido-2-deoxy-3,5:6,7-di-O-isopropylidene-d-glycero-d-ido-heptono-1,4-lactone and 2-azido-2-deoxy-3,5:6,7-di-O-isopropylidene-d-glycero-d-gulo-heptono-1,4-lactone prepared from kinetic and thermodynamic azide displacements of a triflate derived from d-glucoheptonolactone. Azido-γ-lactones are very useful intermediates in the synthesis of iminosugars and polyhydroxylated amino acids. In this study two epimeric azido-heptitols allow biotechnological transformations via Izumoring techniques to 8 of the 16 possible homonojirimycin analogues, 5 of which were isolated pure because of the lack of stereoselectivity of the final reductive amination. A side-by-side glycosidase inhibition profile of 11 of the possible 16 HNJ stereoisomers derived from d-glucose and d-mannose is presented.


Subject(s)
1-Deoxynojirimycin/analogs & derivatives , Azides/chemistry , Glucose/chemistry , Lactones/chemistry , Thermodynamics , 1-Deoxynojirimycin/chemistry , Kinetics , Models, Molecular , Molecular Conformation , Stereoisomerism
2.
Org Lett ; 14(8): 2050-3, 2012 Apr 20.
Article in English | MEDLINE | ID: mdl-22472134

ABSTRACT

Although there are 32 6-azidoheptitols, there are only 16 homonojirimycin (HNJ) stereoisomers. Two epimeric azidoalditols derived from d-mannose allow the synthesis in water of eight stereoisomers of HNJ.


Subject(s)
1-Deoxynojirimycin/analogs & derivatives , Mannose/chemistry , 1-Deoxynojirimycin/chemical synthesis , 1-Deoxynojirimycin/chemistry , Euphorbiaceae/chemistry , Molecular Structure , Stereoisomerism
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