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Molbank 2016, 2016(4), M916; doi:10.3390/M916

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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Author to whom correspondence should be addressed.
Academic Editor: Norbert Haider
Received: 5 October 2016 / Revised: 3 November 2016 / Accepted: 7 November 2016 / Published: 11 November 2016
(This article belongs to the Section Organic Synthesis)
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Abstract

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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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

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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