Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 124, Issue 25, Pages 7343-7352Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja025639c
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- NCRR NIH HHS [1 S10 RR10444] Funding Source: Medline
- NIGMS NIH HHS [GM-58833] Funding Source: Medline
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The C2-hydroxyglycosylation reaction employing the reagent combination of a diaryl sulfoxide and triflic anhydride offers a novel method for glycal assembly whereby a hydroxyl functionality is stereoselectively installed at the C2-position of a glycal donor with concomitant glycosylation of a nucleophilic acceptor. Mechanistic investigations into this reaction revealed a novel process for sulfonium-mediated oxidation of glycal enol ethers in which the sulfoxide oxygen atom is stereoselectively transferred to the C2-position of the glycal. O-18-labeling studies revealed that the S-to-C2 oxygen-transfer process involves initial formation of a C1 - O linkage followed by O-migration to C2, leading to the generation of an intermediate glycosyl 1,2-anhydropyranoside that serves as an in situ glycosylating agent. These findings are consistent with the initial formation of a C2-sulfonium-C1-oxosulfonium pyranosyl species upon activation of the glycal donor with Aryl(2)SO.Tf2O.
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