Substrate-Controlled Direct α-Stereoselective Synthesis of Deoxyglycosides from Glycals Using B(C 6 F 5 ) 3 as Catalyst

Abhijit Sau, Carlos Palo-Nieto, M Carmen Galan*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

19 Citations (Scopus)
182 Downloads (Pure)

Abstract

B(C 6 F 5 ) 3 enables the metal-free unprecedented substrate-controlled direct α-stereoselective synthesis of deoxyglycosides from glycals. 2,3-Unsaturated α-O-glycoside products are obtained with deactivated glycals at 75 °C in the presence of the catalyst, while 2-deoxyglycosides are formed using activated glycals that bear no leaving group at C-3 at lower temperatures. The reaction proceeds in good to excellent yields via concomitant borane activation of glycal donor and nucleophile acceptor. The method is exemplified with the synthesis of a series of rare and biologically relevant glycoside analogues.

Original languageEnglish
Pages (from-to)2415-2424
Number of pages10
JournalJournal of Organic Chemistry
Volume84
Issue number5
Early online date15 Feb 2019
DOIs
Publication statusPublished - 1 Mar 2019

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