Synthesis and nmr characterisation of methyl mono- and DI-0-α-L-rhamnopyranosyl-α-d-glucopyranosiduronic acids

Article abstract of DOI:10.1080/07328309908543980

The synthesis and NMR characterisation of methyl mono- and di-O-α-L-rhamnopyranosyl-α-D-glucopyranosiduronic acids 1-6 are described. Two commercial starting products were used: methyl α-D-glucopyranoside 7 for the preparation of 1 and 2, and methyl (R)-4,6-O-benzylidene-α-D-glucopyranoside 8 for 3-6. Oxidation reaction of the hydroxymethyl group of glucose to a carboxylic acid group was performed by sodium hypochlorite 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO)-mediated procedure after the coupling reaction. Glycosylation was carried out using the trichloroacetimidate approach with trimethylsilyl trifluoromethanesulfonate (TMSOTf) as promoter, resulting in a completely stereoselective formation of the a glycosyl linkage.

Full text of DOI:10.1080/07328309908543980

Journal of Carbohydrate Chemistry
ISSN: 0732-8303 (Print) 1532-2327 (Online) Journal homepage: http://www.tandfonline.com/loi/lcar20
Synthesis and NMR Characterisation of Methyl
Mono- and Di-O-α-L-Rhamnopyranosyl-α-D-
Glucopyranosiduronic Acids
Chiara Laura Battistelli , Cristina De Castro , Alfonso Iadonisi , Rosa
Lanzetta , Lorenzo Mangoni & Michelangelo Parrilli
To cite this article: Chiara Laura Battistelli , Cristina De Castro , Alfonso Iadonisi , Rosa
Lanzetta , Lorenzo Mangoni & Michelangelo Parrilli (1999) Synthesis and NMR Characterisation
of Methyl Mono- and Di-O-α-L-Rhamnopyranosyl-α-D-Glucopyranosiduronic Acids, Journal of
Carbohydrate Chemistry, 18:1, 69-86, DOI: 10.1080/07328309908543980
To link to this article: http://dx.doi.org/10.1080/07328309908543980
Published online: 07 Mar 2008.
Submit your article to this journal
Article views: 74
View related articles
Citing articles: 4 View citing articles
Full Terms & Conditions of access and use can be found at
http://www.tandfonline.com/action/journalInformation?journalCode=lcar20
Download by: [Nanyang Technological University]
Date: 30 May 2016, At: 09:16