Protecting Groups (PG)

Protecting Groups (PG). General Considerations Avoid undesired side reaction PGs have to be Easily introduced and safely removed Stable in reaction conditions Orthogonal Which Groups need protection? If R contains NH2, OH, SH, COOH or other reactive functionalities 2. Review: Albericio et al., Chem. Rev., 2009, 109, 2455. Amine PGs Most common Introduction Fmoc Cl Boc2O. Removal Piperidine TFA. Stable Acidic conditions, Basic conditions, Hydrogenation Hydrogenation Orthogonal Boc, Z, Trt, Alloc Fmoc, Z, Trt, Alloc 3. Amine PGs Amino Acids: Lysine Introduction Cbz2O, Cbz Cl Alloc2O, Alloc Cl ivDde OH. Removal H2 Pd(PPh3), PhSiH3 2% N2H4. Stable Basic and Acidic Basic and Acidic Basic and Acidic conditions conditions conditions, Hydrogenation Orthogonal Boc, Fmoc, Trt Boc, Fmoc, Trt Boc, Fmoc, Z, Trt, Alloc Other Protecting group : Boc 4.

Other protecting group: Boc Amine PGs Introduction Cbz 2 O, Cbz‐Cl Alloc 2 O, Alloc‐Cl ivDde‐OH Removal H 2 Pd(PPh 3), PhSiH 3 2% N 2 H 4 Stable Basic and Acidic conditions Basic and Acidic conditions Basic and Acidic conditions, Hydrogenation Orthogonal Boc, Fmoc, Trt Boc, Fmoc, Trt Boc, Fmoc, Z, Trt, Alloc 4

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