Isolation of a sultone as an unusual acetolysis product

Isolation of a sultone as an unusual acetolysis product

Acetolysis of methyl 5,6-di-O-acetyl-2,3-O-isopropylidene-β-l-gulofuranoside has yielded a sultone, 4-(1,2,5,6-tetra-O-acetyl-β-l-gulofuranos-3-yl)-6-methyl-1,2-oxathiin 2,2-dioxide (2) whose structure was determined by X-ray diffraction. 1H and 13C NMR spectral properties of 2 are presented togethe...

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Veröffentlicht in:Carbohydrate research 2011-05, Vol.346 (6), p.854-857
Hauptverfasser: Craig, Donald C., Stevens, John D.
Format: Artikel
Sprache:eng
Schlagworte:
Acetals
Acetolysis
carbon
Furanose
Magnetic Resonance Spectroscopy
Molecular Structure
Naphthalenesulfonates - chemical synthesis
Naphthalenesulfonates - chemistry
NMR
nuclear magnetic resonance spectroscopy
spectral analysis
stable isotopes
Sultone
X-ray crystallography
X-Ray Diffraction
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Zusammenfassung:Acetolysis of methyl 5,6-di-O-acetyl-2,3-O-isopropylidene-β-l-gulofuranoside has yielded a sultone, 4-(1,2,5,6-tetra-O-acetyl-β-l-gulofuranos-3-yl)-6-methyl-1,2-oxathiin 2,2-dioxide (2) whose structure was determined by X-ray diffraction. 1H and 13C NMR spectral properties of 2 are presented together with a rationale for its formation. Preparation and properties of the related α-d-mannofuranos-3-yl compound 4 are described.
ISSN:0008-6215
1873-426X
DOI:10.1016/j.carres.2011.01.035