MICHAEL-type additions in the synthesis of α-O- and -S-2-deoxyglycosides

Katja Michael, Horst Kessler

Research output: Contribution to journalArticlepeer-review

28 Scopus citations

Abstract

O- and S-Nucleophiles including galactose, serine and cysteine derivatives undergo MICHAEL-type additions to hex-1-en-3-uloses to furnish stereoselectivity the α-2-deoxy-ulosides. The keto function at C-3 can be reduced stereoselectively with NaBH4. Both configurations can be obtained depending on the presence or absence of CeCl3. Glycosylation takes place either base catalyzed with DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) or KCN/18-crown-6 or acid catalyzed by ZnI2.

Original languageEnglish
Pages (from-to)3453-3456
Number of pages4
JournalTetrahedron Letters
Volume37
Issue number20
DOIs
StatePublished - 13 May 1996

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