An expeditious route to Streptococci and Enterococci glycolipids via ring-opening of 1,2-anhydrosugars with protic acids

Article abstract of DOI:10.1080/07328309808002906

1,2-Anhydroglucose 6 reacts smoothly and with a high degree of stereoselectivity with a variety of carboxylic and phosphoric acids resulting in the formation of the predominantly β-oriented 1-O-acyl and 1-O-phosphorylglucoses 7-17. This methodology has been successfully applied in the construction of glycolipids 1a,b. Ring-opening of the 1,2-anhydroglucose derivative 19 with benzoic acid furnished exclusively the β-aligned key intermediate 20. Subsequent ICDT-assisted chemoselective α-glucosylation of 20 with thioethyl donor 21, followed by glycosidation of kojibiosyl benzoate 22 with glycerol acceptor 23 gave the fully protected α-diglucosyl glycerol derivative 25, which upon desilylation (→28), acylation (→29 or 30) and deprotection afforded the target glycolipids 1a-b in high overall yield.

Full text of DOI:10.1080/07328309808002906

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Journal of Carbohydrate Chemistry
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An Expeditious Route to Streptococci
and Enterococci Glycolipids Via Ring-
Opening of 1,2-Anhydrosugars with
Protic Acids
C. M. Timmers a , N. C.R. van Straten a , G. A. van der Marel a & J.
H. van Boom a
a Leiden Institute of Chemistry, Gorlaeus Laboratories, Leiden
University, P.O. Box 9502, 2300 RA, Leiden, The Netherlands
Version of record first published: 15 Aug 2006.
To cite this article: C. M. Timmers , N. C.R. van Straten , G. A. van der Marel & J. H. van Boom
(1998): An Expeditious Route to Streptococci and Enterococci Glycolipids Via Ring-Opening of 1,2-
Anhydrosugars with Protic Acids, Journal of Carbohydrate Chemistry, 17:3, 471-487
To link to this article: http://dx.doi.org/10.1080/07328309808002906
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