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PROTECTING GROUPS IN ORGANIC SYNTHESIS

PROTECTING GROUPS IN ORGANIC SYNTHESIS1 Challenges in ORGANIC :56 PMProtecting GROUPS : A Necessary Evil3 Note,however, :56 PMProtecting GROUPS in ORGANIC SynthesisWhat is a PROTECTING group?Aprotectinggroup(PG)isamolecularfr ameworkthatisintroducedontoaspecificfunc tionalgroup(FG) :56 PMQualities of a Good PROTECTING Group in ORGANIC Synthesis5 Agoodprotectinggroupshouldbesuchthat:(a) Itshouldbereadily,butselectivelyintroduc edtothedesiredfunctionalgroupinapoly-fun ctionalmolecule.(b)Itshouldbestable/resi stanttothereagentsemployedinsubsequentre actionstepsinwhichthegroupbeingmasked(pr otected)isdesiredtoremaindeactivated(pro tected).(c) :56 PMProtecting GROUPS in ORGANIC :56 PMProtecting GROUPS for :(a)Silylether PROTECTING GROUPS (b) Acetalprotecting groupsThese protections replace the acidic proton on an alcohol with an unreactive ether GROUPS for AlcoholsFormation81:56 PMProtecting GROUPS for AlcoholsExampleTert-Butyldimethylsilyl ethers (TBDMS)91:56 PMProtecting GROUPS for Alcohols(SilylProtecting GROUPS )CleavageFluoride sources:Tetrabutylammonium fluoride, Bu4N+F-(TBAF)Pyridine-HFHydrofluoric acid (HF)Ammonium fluoride NH4+F-101:56 PMProtecting GROUPS for Alcohols(SilylProtecting GROUPS )Synthetic Applications of Silyl PROTECTING Groups111:56 GROUPS for Alcohols(SilylProtecting GROUPS )Synthetic Applications of Silyl PROTECTING :56

Protecting Groups: A Necessary Evil 3 Note, however, that each protecting group incorporated in a multi-step synthesis increases the synthesis by two non-productive steps reducing the overall yield and efficiency of the synthesis.

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