Transcription of PROTECTING GROUPS IN ORGANIC SYNTHESIS
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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 PMProtecting GROUPS for Alcohols(Benzyl ether PROTECTING Grou)
Protecting Groups in Organic Synthesis 6 ... Acetal Protecting Group Acid catalysed hydrolysis (dilute HCl or AcOH / H 2 O or TFA/ H 2 O or p- ... Protecting Groups for Amino Groups (Carbamate Protecting Groups) Formation Tert-Butyloxycarbonyl Protecting Group (BOC) 1:56 PM 26 Example.
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PROTECTING GROUPS, Acid, Amino Groups, Amino, Coupling Reagents, Amino acid, Amino protecting groups, ORTHOGONALITY OF PROTECTING GROUPS, Protecting, Groups, Solid Phase Peptide Synthesis, Strategies and Resins, Methods in Peptide Synthesis. Part, Amino Acid-Protecting Groups, Protecting Groups Handout A