Repozytorium

Macrocyclic receptors containing sucrose skeleton.

Autorzy

Sławomir Jarosz

Arkadiusz Listkowski

Bartosz Lewandowski

Zbigniew Ciunik

Anna Brzuszkiewicz

Rok wydania

2005

Czasopismo

Tetrahedron

Numer woluminu

61

Strony

8485-8492

DOI

10.1016/j.tet.2005.06.046

Kolekcja

Naukowa

Język

Angielski

Typ publikacji

Artykuł

Streszczenie

Crown ether analogues with incorporated sucrose unit were prepared by reaction of 1′,2,3,3′,4,4′-hexa-O-benzylsucrose with polyethylene ditosylates in up to 52% yield. Stability constants of their complexes with Li+, Na+, K+, NH4+ were determined by the NMR titration method. The macrocycles were also tested as catalysts in the enantioselective Michael reaction, but with little success (ee up to only 22%). The macrocycle containing nitrogen in the ring was also prepared in good yield. All prepared macrocycles were easily converted into the free sucrose crowns (H2/Pd/C) without destroying the (very labile) glycosidic bond. The crystal structure of the selected receptor was determined.

Słowa kluczowe

Sucrose, Chiral receptors, Crown ether analogues

Adres publiczny

https://doi.org/10.1016/j.tet.2005.06.046

Strona internetowa wydawcy

http://www.elsevier.com

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