Document Detail


De novo asymmetric synthesis of all-D-, all-L-, and D-/L-oligosaccharides using atom-less protecting groups.
MedLine Citation:
PMID:  22780712     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Oligosaccharide synthesis is hindered by the need for multiple steps as well as numerous selective protections and deprotections. Herein we report a highly efficient de novo route to various oligosaccharide motifs, of use for biological and medicinal structure activity studies. The key to the overall efficiency is the judicious use of asymmetric catalysis and synthetic design. These green principles include the bidirectional use of highly stereoselective catalysis (Pd(0)-catalyzed glycosylation/post-glycosylation). In addition, the chemoselective use of C-C and C-O π-bond functionality, as atom-less protecting groups as well as an anomeric directing group (via a Pd-π-allyl), highlights the atom-economical aspects of the route to a divergent set of natural and unnatural oligosaccharides (i.e., various d-/l-diastereomers of oligosaccharides as well as deoxysugars which lack C-2 anomeric directing groups). For example, in only 12 steps, the construction of a highly branched heptasaccharide with 35 stereocenters was accomplished from an achiral acylfuran.
Authors:
Ravula Satheesh Babu; Qian Chen; Sang-Woo Kang; Maoquan Zhou; George A O'Doherty
Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural; Research Support, U.S. Gov't, Non-P.H.S.     Date:  2012-07-16
Journal Detail:
Title:  Journal of the American Chemical Society     Volume:  134     ISSN:  1520-5126     ISO Abbreviation:  J. Am. Chem. Soc.     Publication Date:  2012 Jul 
Date Detail:
Created Date:  2012-07-25     Completed Date:  2012-11-27     Revised Date:  2013-07-31    
Medline Journal Info:
Nlm Unique ID:  7503056     Medline TA:  J Am Chem Soc     Country:  United States    
Other Details:
Languages:  eng     Pagination:  11952-5     Citation Subset:  IM    
Affiliation:
Department of Chemistry and Chemical Biology, Northeastern University, Boston, Massachusetts 02115, USA.
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MeSH Terms
Descriptor/Qualifier:
Catalysis
Glycosylation
Green Chemistry Technology
Oligosaccharides / chemical synthesis*,  chemistry
Palladium / chemistry
Stereoisomerism
Grant Support
ID/Acronym/Agency:
GM090259/GM/NIGMS NIH HHS; R01 GM090259/GM/NIGMS NIH HHS
Chemical
Reg. No./Substance:
0/Oligosaccharides; 7440-05-3/Palladium
Comments/Corrections

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