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2-C-Alkynyl and 2-C-cis-Alkenyl β-Mannosides with Acetal Protected γ-Aldehyde Functionality via 2-Uloside Alkynylation and Lindlar Hydrogenation

Institute of Organic Chemistry, University of Tübingen, Auf der Morgenstelle 18, 72076 Tübingen, Germany
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Academic Editor: Norbert Haider
Molbank 2016, 2016(4), M916; https://doi.org/10.3390/M916
Received: 5 October 2016 / Revised: 3 November 2016 / Accepted: 7 November 2016 / Published: 11 November 2016
(This article belongs to the Section Organic Synthesis)
Benzyl 3,4,6-tri-O-benzyl-β-d-arabino-hexos-2-ulo-1,5-pyranoside was subjected to manno-selective ketone alkynylation with propiolaldehyde dibenzyl acetal, resulting in the formation of a 2-C-alkynyl β-mannoside bearing a γ-dibenzyl acetal functionality. Subsequent transacetalization of the acetal moiety with methanol and 1,3-dihydroxypropane and acetylation of position 2, respectively, gave 4 different 2-C-alkynyl branched mannosides. Lindlar hydrogenation of the latter under optimized conditions in dimethylformamide afforded a series of 2-C-cis-alkenyl mannosides. X-ray molecular structures of benzyl 3,4,6-tri-O-benzyl-β-d-arabino-hexos-2-ulo-1,5-pyranoside and of the branched glycoside benzyl 3,4,6-tri-O-benzyl-2-C-((Z)-3,3-dibenzyloxyprop-1-en-1-yl)-β-d-mannopyranoside are reported. View Full-Text
Keywords: branched carbohydrates; alkynylation; alkynes; cis-alkenes; Lindlar hydrogenation; partial hydrogenation; β-mannosides; 2-ulosides branched carbohydrates; alkynylation; alkynes; cis-alkenes; Lindlar hydrogenation; partial hydrogenation; β-mannosides; 2-ulosides
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Borowski, D.; Menzel, M.; Ziegler, T. 2-C-Alkynyl and 2-C-cis-Alkenyl β-Mannosides with Acetal Protected γ-Aldehyde Functionality via 2-Uloside Alkynylation and Lindlar Hydrogenation. Molbank 2016, 2016, M916.

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