Synthesis of 3-Amino-4-(Hydroxymethyl)-β-Lactam Branch Point and Its Late-Stage C4 Functionalization with Ceftaroline-Sidechain Monobactams and Their Biological Evaluation
Two alternative routes to 3-amino-4-(hydroxymethyl)-2-azetidinone are compared, a synthon carrying handles at N1, C3 and C4, starting from ethyl glyoxylate and from (R)-glyceraldehyde acetonide, which replaces a low-yielding NaBH4 ester reduction with a near-quantitative oxidative cleavage/reduction sequence.