Hafnium(IV) tetratriflate in selective reductive carbohydrate benzylidene acetal opening reaction and direct silylation reaction

Hafnium(IV) tetratriflate was shown to be an effective catalyst for the regioselective reductive benzylidene ring opening with concurrent silylation reaction. The synthetic conditions were optimized, and the scope and limitations were identified. In addition to glucose and glycosamine derivatives, m...

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Bibliographic Details
Published in:Tetrahedron letters 2013-12, Vol.54 (50), p.6838-6840
Main Authors: Manabe, Shino, Ito, Yukishige
Format: Article
Language:English
Subjects:
Carbohydrates
Derivatives
Deuteration
Galactose
Glucose
Mannose
Reduction
Regioselectivity
Ring opening
Silylation
Tetrahedrons
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Summary:Hafnium(IV) tetratriflate was shown to be an effective catalyst for the regioselective reductive benzylidene ring opening with concurrent silylation reaction. The synthetic conditions were optimized, and the scope and limitations were identified. In addition to glucose and glycosamine derivatives, mannose and galactose were successfully employed as substrates. Various protecting groups such as acetyl, allyl, and benzyl were found to be stable under the reaction conditions. By using a deuterated reducing reagent, the reaction was deduced to proceed via an SN1 mechanism.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2013.10.011