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  • Title: Synthesis of alkylated sugar amino acids: conformationally restricted L-Xaa-L-Ser/Thr mimics.
    Author: Risseeuw MD, Mazurek J, van Langenvelde A, van der Marel GA, Overkleeft HS, Overhand M.
    Journal: Org Biomol Chem; 2007 Jul 21; 5(14):2311-4. PubMed ID: 17609763.
    Abstract:
    Two synthetic strategies for the generation of delta-substituted pyranoid sugar amino acids (SAAs) are evaluated. The first employs chiral nonracemic tert-butane sulfinamides as key reagents. Regardless of the stereochemistry of the applied sulfinamide, the product formed has a stereochemistry resembling that of a d amino acid at C7. Direct Grignard reaction on formyl-tetra-O-benzyl-beta-D-C-glucopyranoside in the second strategy and subsequent Mitsunobu inversion, yields the l,l-dipeptide isosters.
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