Solid-phase organic synthesis amides

Photolabile linkers play an important role in solid-phase organic synthesis (SPOS) due to their stability under both acidic and basic conditions. The ONb photolabile linker was modified to improve cleavage rates and yields Fmoc-Tos-OFI was released in 87% yield after 23 h (Scheme 4) [24]. Specifically, the primary alcohol was changed to a secondary benzylic alcohol and the attachment to the resin was through an alkyl chain as opposed to an amide function. Linker 20 was used for the production of carboxylic acids or carbohydrates. A second example... 

SCHEME 10 Solid phase organic synthesis (SPOS) of benzimidazole from Rink amide resin. 

Sieber P (1987) A new acid-labile anchor group for the solid-phase synthesis of C-terminal peptide amides by the Fmoc method. Tetrahedron Lett 28 2107-2110 Mende F, Seitz O (2011) 9-Fluorenylmethoxycarbonyl-based solid-phase synthesis of peptide a-thioesters. Angew Chem Int Ed 50 1232-1240 Giiillier F, Grain D, Bradley M (2000) Linkers and cleavage strategies in solid-phase organic synthesis and combinatorial chemistry. Chem Rev 100 2091-2158... 

Lawrence, R. M. Biller, S. A. Fryszman, O. M. Poss, M. A. Automated Synthesis and Purification of Amides Exploitation of Automated Solid Phase Extraction in Organic Synthesis, Synthesis, 1997, 5, 553. 

Lawrence RM, Biller SA, Fryszman OM, Poss MA, Automated synthesis and purification of amides exploitation of automated solid phase extraction in organic synthesis, Synthesis, 553-558, 1997. 

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