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The 2,3-epoxide, a donor in lanthanide shift-reagent studies of carbohydrate systems; the x-ray structure of methyl 2,3-anhydro-4,6-O-benzylidene-β-d-mannopyranoside

✍ Scribed by Desmond Cunningham; Noel Gavin; Elizabeth Lee; Patrick McArdle; John O'Callaghan; Timothy Higgins

Publisher
Elsevier Science
Year
1988
Tongue
English
Weight
584 KB
Volume
177
Category
Article
ISSN
0008-6215

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✦ Synopsis

Lanthanide-induced shifts in the 'H-n.m.r. spectra of the methyl 2,3-anhydro-4,6-0-benzylidene-D-hexopyranosides

[manno (1 and 5), allo (2 and 6), gulo (3 and 7), Q! and 0, respectively, and wtalo (4)] have been measured. The observed shift data for the cx-manno, @-allo, and fl-gulo epoxides were in good agreement with those calculated for the OH, conformation of the pyranoid ring using a single-site model. Shifts calculated for the "H, conformation of the @manno epoxide using a two-site model were in excellent agreement with the observed shift data. The '3Cn.m.r. spectra were assigned by decoupling techniques, and n.m.r. line-shifts ('H and 13C) induced by the shift reagents were used in some cases for complete assignment of signals. The solid-state structure of methyl 2,3-anhydro-4,6-O-benzylidene-/3-D-mannopyranoside (5) has been determined by X-ray crystallographic analysis.

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