Glibstrup Emil, Pedersen Christian Marcus
Department of Chemistry, University of Copenhagen, Universitetsparken 5, 2100 Copenhagen O, Denmark.
Beilstein J Org Chem. 2018 Nov 8;14:2805-2811. doi: 10.3762/bjoc.14.258. eCollection 2018.
The motif α-D-GalNAc-(1-3)-D-GalNAc 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--protected acceptor and that both regio- and anomeric selectivity is enhanced by bulky 6--protective groups. The acceptors and donors are made from common building blocks, limiting protective manipulations, and in this context, unavoidable side reactions.
基序α-D-氨基半乳糖-(1-3)-D-氨基半乳糖在自然界中非常常见，因此其合成具有高度相关性。已经对其叠氮基前体的合成进行了研究，并在步骤、产率和选择性方面进行了优化。已发现，与使用4-位保护的受体相比，3,4-二醇受体的糖基化具有优势，并且庞大的6-位保护基团可增强区域选择性和端基异构选择性。受体和供体由常见的结构单元制成，限制了保护操作以及在这种情况下不可避免的副反应。
