594
3
Chemical Glycosylation Reactions
⊡ Figure 4
Multibranched hexafuranoarabinan of Mycobacterium species
cafuranoarabinan of Mycobacterium species, 176a ( > Fig. 3). The final NPG→trichloroacetimidate transformation (176a→176b) made possible the coupling of this arabinan segment
to an oligomannan acceptor, thus resulting in the synthesis of the largest heterooligosaccharide
to date, a 28-mer arabinomannan [91].
n-Pentenyl arabinofuranosides have also been used by Seeberger and co-workers in the
final stages of their synthesis of a 12-mer component of Mycobacterium tuberculosis [92].
n-Pentenyl arabinan hexasaccharide 177a, was transformed to the corresponding trichloroacetimidate 177b and coupled with a mannan hexasaccharide acceptor to yield the sought
arabinomannan dodecasaccharide ( > Fig. 4).
⊡ Scheme 25
NPGs as glycosyl donors in intramolecular aglycon delivery
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