Synthesis, crystal structure, and reactivity of a D-xylose based oxepine.
The synthesis and X-ray crystal structure of a D-xylose-based oxepine are reported. The oxepine was prepared from 2,3,4-tri-O-benzyl-D-xylose by the three-step sequence (Wittig olefination, vinyl ether formation, and ring closing metathesis) we recently reported. Epoxidation of this cyclic enol ether using dimethyldioxirane (DMDO) gave 1,2-anhydro-beta-D-idoseptanose, which was trapped by a number of nucleophiles to give alpha-idoseptanosides. The stereochemistry of epoxidation was assigned based on product analysis. Spectroscopic data of methyl 2,3,4,5-tetra-O-acetyl-alpha-D-idoseptanoside, derived from the methanolysis product 11, was compared to data of its enantiomer, the known methyl 2,3,4,5-tetra-O-acetyl-alpha-L-idoseptanoside.
Peczuh
Mark W
MW
Department of Chemistry, The University of Connecticut, 55 North Eagleville Road, Storrs, CT 06269, USA. peczuh@uconn.edu
Snyder
Nicole L
NL
Sean Fyvie
W
W
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002241:Carbohydrates / Q000737:chemistry; D018360:Crystallography, X-Ray; D004852:Epoxy Compounds / Q000737:chemistry; D006031:Glycosylation; D008956:Models, Chemical; D008958:Models, Molecular; D008969:Molecular Sequence Data; D010082:Oxepins / Q000737:chemistry*; D013053:Spectrophotometry; D013237:Stereoisomerism; D014994:Xylose / Q000737:chemistry*
D002241:Carbohydrates; D004852:Epoxy Compounds; D010082:Oxepins; D014994:Xylose; C064455:dimethyldioxirane