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

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

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 m...

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Bibliographic Details
Main Authors: Daniel Borowski, Melchior Menzel, Thomas Ziegler
Format: Article
Language:English
Published: MDPI AG 2016-11-01
Series:Molbank
Subjects:
branched carbohydrates
alkynylation
alkynes
cis-alkenes
Lindlar hydrogenation
partial hydrogenation
β-mannosides
2-ulosides
Online Access:http://www.mdpi.com/1422-8599/2016/4/M916

Internet

http://www.mdpi.com/1422-8599/2016/4/M916

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