NDLI: A 3,4-trans-Fused Cyclic Protecting Group Facilitates α-Selective Catalytic Synthesis of 2-Deoxyglycosides

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A 3,4-trans-Fused Cyclic Protecting Group Facilitates α-Selective Catalytic Synthesis of 2-Deoxyglycosides

Content Provider	Scilit
Author	Balmond, Edward I. Benito-Alifonso, David Coe, Diane M. Alder, Roger W. McGarrigle, Eoghan M. Galan, M. Carmen
Copyright Year	2014
Description	Journal: Angewandte Chemie International Edition A practical approach has been developed to convert glucals and rhamnals into disaccharides or glycoconjugates with high α-selectivity and yields (77–97 %) using a trans-fused cyclic 3,4-O-disiloxane protecting group and $TsOH⋅H_{2}$O (1 mol %) as a catalyst. Control of the anomeric selectivity arises from conformational locking of the intermediate oxacarbenium cation. Glucals outperform rhamnals because the C6 side-chain conformation augments the selectivity.
Related Links	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4499252/pdf
Ending Page	8194
Page Count	5
Starting Page	8190
ISSN	14337851
e-ISSN	15213773
DOI	10.1002/anie.201403543
Journal	Angewandte Chemie International Edition
Issue Number	31
Volume Number	53
Language	English
Publisher	Wiley-Blackwell
Publisher Date	2014-06-20
Access Restriction	Open
Subject Keyword	Journal: Angewandte Chemie International Edition Organic Chemistry Conformation Analysis Homogeneous Catalysis Protecting Groups Synthetic Methods
Content Type	Text
Resource Type	Article
Subject	Chemistry Catalysis

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