Synthesis of α-D-GalpN₃-(1-3)-D-GalpN₃: α- and 3-O-selectivity using 3,4-diol acceptors

TY - JOUR

T1 - Synthesis of α-D-GalpN3-(1-3)-D-GalpN3

T2 - α- and 3-O-selectivity using 3,4-diol acceptors

AU - Glibstrup, Emil

AU - Pedersen, Christian Marcus

PY - 2018/11/8

Y1 - 2018/11/8

N2 - The motif α-D-GalpNAc-(1-3)-D-GalpNAc 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.

AB - The motif α-D-GalpNAc-(1-3)-D-GalpNAc 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.

U2 - 10.3762/bjoc.14.258

DO - 10.3762/bjoc.14.258

M3 - Journal article

C2 - 30498530

SN - 2195-951X

VL - 14

SP - 2805

EP - 2811

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

ER -