Synthetic approaches towards novel N-protected γ- and δ-furanoid sugar amino acids (SAAs) or tetrahydrofuran amino acids were developed. SAAs have emerged as valuable building blocks for the syntheses of peptide mimetics, so-called carbopeptoids. 3-C-Substituted 1,2-O-isopropylidene-α-D-allofuranose derivatives have been used as starting materials. The designed SAAs possess either cis- or trans-orientated C(3)-aminomethyl and C(4)- or C(5)-carboxylic acid functional groups attached to the 1,2-O-isopropylidene furanoid core, thus providing different spatial arrangement. Short-chain homooligomers derived from one γ-SAAs and δ-SAA were synthesized as the initial step towards exploration of novel carbopeptoids. The key intermediates of the presented SAA syntheses can be easily transformed into the molecules containing azide and terminal alkyne moieties and as such can be used for syntheses of 1,2,3-triazole isosters of peptides in the future.