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Glycosylation, 影響donor反應速率的因素, Donor, Acceptor, Solvent - Coggle Diagram
Glycosylation
Fischer Glycosylation
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Trap在furan的方法
kinetic control的Fischer
5-exo-trig, Bürgi–Dunitz angle (107°)
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SN2
sugar (1-OH, n-OP) + ROTf → sugar (1-OR, n-OP)
stereoselectivity
controlled by base, solvent, temp., PG
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sugar (1-halides, n-OP) + NaOR or NaSR
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影響donor反應速率的因素
Armed/Disarmed
EWD形成disarmed，EDG形成armed
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High electronegative atoms (e.g., F) are EWG.
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Donor
O
trichloroacetimidate
stable, easily prepared from reducing sugar
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acetimidate
not stable, not easily prepared and purified
halides
I
more reactive, don't need activator
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S
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thio
activator: NIS/TfOH, NIS/AgOTf, MeOTf, IDPC, iodine...
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Others
Se, in situ, glycal epoxides, oxidation addition to glycals
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