Protic Acid (HClO4 Supported on Silica Gel)-Mediated Synthesis of 2,3-Unsaturated-O-glucosides and a Chiral Furan Diol from 2,3-Glycals

Perchloric acid supported on silica gel acts as an excellent reagent system in converting glucals into 2,3-unsaturated-O-glucosides in good to excellent yields in short reaction time with good α selectivity. Primary, secondary, and allylic alcohols, phenols, and thiols react with 3,4,6-tri-O-acetyl...

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Veröffentlicht in:	Journal of organic chemistry 2004-09, Vol.69 (18), p.6137-6140
Hauptverfasser:	Agarwal, Aditi, Rani, Shikha, Vankar, Yashwant D
Format:	Artikel
Sprache:	eng
Schlagworte:	Calcium Gluconate - chemistry Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides Carbohydrates. Nucleosides and nucleotides Catalysis Chemistry Exact sciences and technology Galactose - analogs & derivatives Galactose - chemistry Glucosides - chemical synthesis Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Indicators and Reagents Molecular Structure Organic chemistry Perchlorates - chemistry Preparations and properties Silica Gel Silicon Dioxide - chemistry
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Beschreibung
Zusammenfassung:	Perchloric acid supported on silica gel acts as an excellent reagent system in converting glucals into 2,3-unsaturated-O-glucosides in good to excellent yields in short reaction time with good α selectivity. Primary, secondary, and allylic alcohols, phenols, and thiols react with 3,4,6-tri-O-acetyl glucal with equal ease. In addition to this, a chiral furan diol is obtained from unprotected d-glucal or d-galactal in good yields.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo049415j