TY  - JOUR
A1  - Pimpalpalle, Tukaram M.
A1  - Yin, Jian
A1  - Linker, Torsten
T1  - Barton radical reactions of 2-C-branched carbohydrates
JF  - Organic & biomolecular chemistry : an international journal of synthetic, physical and biomolecular organic chemistry
N2  - Barton esters have been introduced into the side chain of carbohydrates with high yields in only a few steps from easily available glycals. Their radical reactions afford 2-C-methyl and 2-C-bromomethyl hexoses, pentoses and disaccharides in good yields in analytically pure form. Since the Barton esters have been synthesized by an oxidative radical addition and their transformations by reductive radical processes, our results demonstrate the power of such reactions in carbohydrate chemistry.
Y1  - 2012
U6  - https://doi.org/10.1039/c1ob06370g
SN  - 1477-0520
VL  - 10
IS  - 1
SP  - 103
EP  - 109
PB  - Royal Society of Chemistry
CY  - Cambridge
ER  - 
TY  - JOUR
A1  - Yin, Jian
A1  - Linker, Torsten
T1  - Recent advances in the stereoselective synthesis of carbohydrate 2-C-analogs
JF  - Organic & biomolecular chemistry : an international journal of synthetic, physical and biomolecular organic chemistry
N2  - C-branched carbohydrates are of current interest for glycochemistry, are widely found in nature and serve as important subunits in many antibiotics, bacterial polysaccharides and macrolides. Among C-functionalized saccharides, 2-C-branched carbohydrates represent challenging structures for synthetic chemists, since in contrast to C-glycosides they are not easily accessible from glycosyl bromides or other simple precursors. In this perspective we want to summarize recent approaches to 2-C-branched carbohydrates over the past fifteen years. The two main strategies are based on ring-opening of 1,2-cyclopropanated carbohydrates by various reagents, as well as radical additions to glycals and further transformations, developed in our group. Both methods are characterized by high stereoselectivities and good yields and give access to a broad variety of functionalized carbohydrate 2-C-analogs.
Y1  - 2012
U6  - https://doi.org/10.1039/c2ob06529k
SN  - 1477-0520
VL  - 10
IS  - 12
SP  - 2351
EP  - 2362
PB  - Royal Society of Chemistry
CY  - Cambridge
ER  -