TY  - JOUR
A1  - Mai-Linde, Yasemin
A1  - Linker, Torsten
T1  - Radical clock probes to determine carbohydrate radical stabilities
JF  - Organic letters
N2  - Carbohydrate radical stabilities in the 1- and 2-position have been determined by a radical clock approach, starting from cyclopropanated sugars with xanthates as precursors. Various hexoses and pentoses afforded 1-deoxy sugars as main products, indicating that anomeric radicals are more stable than radicals in the 2-position. An additional influence of the configurations on radical stabilities has been observed. Our results should be interesting for the understanding of 1,2-radical rearrangements in carbohydrate chemistry and offer an easy access to deoxy-vinyl sugars.
KW  - stereoselective-synthesis
KW  - convenient synthesis
KW  - chemistry
KW  - cyclopropanation
KW  - mechanism
KW  - glycals
KW  - beta-(acyloxy)alkylrear
KW  - rangement
KW  - sugars
Y1  - 2020
U6  - https://doi.org/10.1021/acs.orglett.0c00111
SN  - 1523-7060
SN  - 1523-7052
VL  - 22
IS  - 4
SP  - 1525
EP  - 1529
PB  - American Chemical Society
CY  - Washington
ER  -