TY - JOUR
T1 - Anomeric Thioglycosides Give Different Anomeric Product Distributions under NIS/TfOH Activation
AU - Trinderup, Helle H.
AU - Sandgaard, Tatjana L.P.
AU - Juul-Madsen, Line
AU - Jensen, Henrik H.
N1 - Publisher Copyright:
© 2022 American Chemical Society. All rights reserved.
PY - 2022/3
Y1 - 2022/3
N2 - The reaction of a series of anomeric thioglycosides with various glycosyl acceptors and N-iodosuccinimide/catalytic triflic acid was investigated with respect to reactivity and anomeric selectivity. In general, β-configured donors were found to give a more β-selective reaction outcome compared to their α-configured counterparts. The relative reactivity of various thioglycosides was measured through competition experiments, and the following order was established: phenyl, tolyl, methyl, ethyl, isopropyl, and 1-adamantyl.
AB - The reaction of a series of anomeric thioglycosides with various glycosyl acceptors and N-iodosuccinimide/catalytic triflic acid was investigated with respect to reactivity and anomeric selectivity. In general, β-configured donors were found to give a more β-selective reaction outcome compared to their α-configured counterparts. The relative reactivity of various thioglycosides was measured through competition experiments, and the following order was established: phenyl, tolyl, methyl, ethyl, isopropyl, and 1-adamantyl.
UR - http://www.scopus.com/inward/record.url?scp=85126140509&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.1c03001
DO - 10.1021/acs.joc.1c03001
M3 - Journal article
C2 - 35239337
AN - SCOPUS:85126140509
SN - 0022-3263
VL - 87
SP - 4154
EP - 4167
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 6
ER -