Abstract
Among cell-adhesion molecules, L-selectin recognizes sulfated sLex with relatively low affinity. Here, we aimed at artificial mimics by synthesizing a set of di- and tri-sulfated galabioses, which may surpass the affinity of sulfated sLex. As a strategy to obtain 3′,6′,6-tri-O-sulfogalabioses, regioselective reductive cleavage of 4,6- and 4′,6′-di-O-benzylidenegalabioses was employed. Two suitably protected galactose precursors were conjugated to yield α and β anomers (48 and 18%, respectively) by using a pentenyl galactoside donor and iodinium di-sym-collidine perchlorate as the catalyst. For synthesizing the 3′,6-di-O-sulfogalabiose, however, a trichloroacetimidate donor was superior (52%) to the pentenyl one (30%).
Original language | English |
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Pages (from-to) | 167-180 |
Number of pages | 14 |
Journal | Carbohydrate Research |
Volume | 335 |
Issue number | 3 |
DOIs | |
Publication status | Published - 08-10-2001 |
Externally published | Yes |
All Science Journal Classification (ASJC) codes
- Analytical Chemistry
- Biochemistry
- Organic Chemistry