Synthesis of a set of di- and tri-sulfated galabioses

Tomoaki Yoshida, Taku Chiba, Takashi Yokochi, Kikuo Onozaki, Tsuyoshi Sugiyama, Izumi Nakashima

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)


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 languageEnglish
Pages (from-to)167-180
Number of pages14
JournalCarbohydrate Research
Issue number3
Publication statusPublished - 08-10-2001

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry


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