6. glycosidic bond formation - not done
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Flashcardsrequirements for chemical activation of anomeric hydroxyl group
good LG at the anomeric position of the glycosylation donor
PGs
what does activation of the donor result in
reactive carbocation intermediate, oxocarbenium ion (O in hexose sugar ring positively charged, X-)
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9 Terms
requirements for chemical activation of anomeric hydroxyl group
good LG at the anomeric position of the glycosylation donor
PGs
what does activation of the donor result in
reactive carbocation intermediate, oxocarbenium ion (O in hexose sugar ring positively charged, X-)
how and what are the two products of the oxocarbenium ion being attacked by an acceptor
attacked from either face of the sugar ring
bottom attack = alpha
top attack = beta
what is formed if the LG does not fully dissociate
a transition state with partial oxocarbenium ion character
what can be used as X (LG)
glycosyl bromide
trichloroacetimidate
thioethers
steps for adding glycosyl bromide as LG
use Ac2O and pyridine to protect all hydroxyl groups
add HBR to make anomeric carbon have Br attached
Note 
Flashcards (29)