Evaluation of Thioglycosides of Kdo as Glycosyl Donor
2007 (English)In: Carbohydrate Research, ISSN 0008-6215, E-ISSN 1873-426X, Vol. 342, no 3-4, 631-637 p.Article in journal (Refereed) Published
The use of Kdo thioglycosides as glycosyl donors using DMTST, IBr/AgOTf and NIS/AgOTf as promoters has been evaluated. Activation at low temperature allowed to escape the formation of 2,3-glycal byproducts to give glycosides in high yield and with good β-anomeric selectivity. The use of diethyl ether as solvent and (especially) isopropylidene acetals as protecting groups improved the α-anomeric selectivity. NIS/AgOTf as promoter surprisingly yielded the 3-iodo-product via the glycal intermediate.
Place, publisher, year, edition, pages
Elsevier , 2007. Vol. 342, no 3-4, 631-637 p.
Thioglycoside donors; Kdo glycosides; Thiophilic promoters
IdentifiersURN: urn:nbn:se:su:diva-25824DOI: 10.1016/j.carres.2006.08.021ISI: 000244548700028OAI: oai:DiVA.org:su-25824DiVA: diva2:200604
Part of urn:nbn:se:su:diva-8942006-03-092006-03-092010-10-04Bibliographically approved