Cross-coupling of propargylated arabinogalactan with 2-bromothiophene.
Novel pharmacologically prospective derivatives of arabinogalactan (a polysaccharide from larch wood) containing acetylenic and thiophene moieties have been obtained in up to 90% yield by cross-coupling of propargylic ethers of arabinogalactan with 2-bromothiophene. The reaction proceeds in the presence of the catalytic system Pd(Ph3P)4/CuBr/LiBr and piperidine in DMSO at 80-85°С. An advantageous feature of the synthesis is that it requires 5-25 times lesser catalytic loading than in common Sonogashira protocols thus making the reaction particularly beneficial to synthesize pharmaceutically-oriented polysaccharides.
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation.
Lidiya N
LN
Parshina
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation.
Lyudmila A
LA
Grishchenko
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation.
Lyudmila I
LI
Larina
Irkutsk State Agricultural Academy, Molodezhny Settlement, 664038 Irkutsk, Russian Federation.
Lyubov N
LN
Novikova
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation. Electronic address: boris_trofimov@irioch.irk.ru.
Boris A
BA
Trofimov
D003208:Concanavalin A / Q000378:metabolism; D005685:Galactans / Q000737:chemistry* / Q000378:metabolism; D020005:Propanols / Q000737:chemistry; D013876:Thiophenes / Q000737:chemistry*
D005685:Galactans; D020005:Propanols; D013876:Thiophenes; D003208:Concanavalin A; C005653:arabinogalactan
2-Bromothiophene; Arabinogalactan functionalization; Ethynyl thiophene; Homocoupling; Propargylated arabinogalactan; Sonogashira reaction