Synthesis of α-D-Gal p N 3 -(1-3)-D-Gal p N 3 : α- and 3- O- selectivity using 3,4-diol acceptors.

Autor: Glibstrup E; Department of Chemistry, University of Copenhagen, Universitetsparken 5, 2100 Copenhagen O, Denmark., Pedersen CM; Department of Chemistry, University of Copenhagen, Universitetsparken 5, 2100 Copenhagen O, Denmark.
Jazyk: angličtina
Zdroj: Beilstein journal of organic chemistry [Beilstein J Org Chem] 2018 Nov 08; Vol. 14, pp. 2805-2811. Date of Electronic Publication: 2018 Nov 08 (Print Publication: 2018).
DOI: 10.3762/bjoc.14.258
Abstrakt: The motif α-D-Gal p NAc-(1-3)-D-Gal p NAc is very common in Nature and hence its synthesis highly relevant. The synthesis of its azido precursor has been studied and optimized in terms of steps, yields and selectivity. It has been found that glycosylation of the 3,4-diol acceptor is an advantage over the use of a 4- O -protected acceptor and that both regio- and anomeric selectivity is enhanced by bulky 6- O -protective groups. The acceptors and donors are made from common building blocks, limiting protective manipulations, and in this context, unavoidable side reactions.
Databáze: MEDLINE