Efficient Synthesis of β-D-Mannosides and β-D-Talosides by Double Parallel or Double Serial Inversion
2007 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 72, no 10, 3694-3701 p.Article in journal (Refereed) Published
A neighboring equatorial ester group plays a highly important role in the Lattrell-Dax (nitrite-mediated) carbohydrate epimerization reaction, inducing the formation of inversion compounds in good yields. On the basis of this effect, efficient synthetic routes to beta-D-mannosides and beta-D-talosides, from the corresponding beta-D-galactosides and beta-D-glucosides, have been designed. The present routes are based on multiple regioselective acylation via the respective stannylene intermediates, followed by inversions to the corresponding manno- and talopyranoside structures by nitrite or acetate substitution. It was found that the ester group was able to induce the inversion of its two neighboring groups in high yields following either a double parallel or a double serial inversion process. By combination of direct inversion, and neighboring- as well as remote-group participation, several beta-D-mannoside and beta-D-taloside derivatives were very conveniently obtained in good yields.
Place, publisher, year, edition, pages
2007. Vol. 72, no 10, 3694-3701 p.
INTRAMOLECULAR AGLYCON DELIVERY; STEREOSELECTIVE-SYNTHESIS; CORE PENTASACCHARIDE; D-MANNOPYRANOSIDES; N-GLYCANS; CHEMOENZYMATIC SYNTHESIS; LINKED GLYCOPROTEINS; PRACTICAL SYNTHESIS; CHEMICAL-SYNTHESIS; NITRITE ANIONS
IdentifiersURN: urn:nbn:se:kth:diva-9886DOI: 10.1021/jo062643oISI: 000246206700013ScopusID: 2-s2.0-34248573311OAI: oai:DiVA.org:kth-9886DiVA: diva2:139846
QC 201007092009-01-272009-01-272016-05-09Bibliographically approved