Synthesis of a C-glycoside analogue of β-D -galactosyl threonine
2003 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 68, no 6, 2506-2509 p.Article in journal (Refereed) Published
A C-linked analogue of β-d-galactosylthreonine has been prepared from 2,3,4,6-tetra-O-benzyl-d-galactopyranolactone (1) in 14 steps. Three stereogenic centers were created during the synthesis, with the anomeric center of the C-glycoside being generated first by addition of a Grignard reagent to 1 and subsequent reduction of the intermediate hemiacetal with triethylsilane. The two stereogenic centers in the threonine moiety were both established by alkylation of Evans' chiral N-acyloxazolidinone enolates.
Place, publisher, year, edition, pages
American Chemical Society (ACS), 2003. Vol. 68, no 6, 2506-2509 p.
IdentifiersURN: urn:nbn:se:umu:diva-4780DOI: 10.1021/jo026758dOAI: oai:DiVA.org:umu-4780DiVA: diva2:144018