Journal
JOURNAL OF CARBOHYDRATE CHEMISTRY
Volume 30, Issue 7-9, Pages 575-586Publisher
TAYLOR & FRANCIS INC
DOI: 10.1080/07328303.2011.610545
Keywords
Glycosylation; Green chemistry; Recyclable solid superacid; Lewis acid site; Calcium chloride
Funding
- Ministry of Education, Culture, Science, and Technology, Japan
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The simple doping of calcium chloride allowed highly improved yields in the glycosylation promoted by sulfated zirconia (SZ) without calcination. It was revealed by means of per-O-benzylated galactose trichloroacetimidate as a model glycosyl donor that this effect depends greatly on the cationic ion radius of used metal chlorides. Temperature-programmed desorption of ammonia (NH3 TPD) and the pyridine IR method showed clearly that coordination of calcium ion provides the SZ surface with newly formed Lewis acidic sites while the Bronsted acid site disappeared, indicating that the enhanced catalytic potency of SZ is due to the increased Lewis acid sites by doping the optimal calcium ions. The present findings might give insight into the relationship between a catalytic mechanism and superacidity of SZ, which is crucial for the design of novel superacid-based catalysts and environmentally benign glycosylation processes.
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