308357-95-1

Upstream product

• 100945-15-1 N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester 
• 308357-97-3 n-propyl 4-formyl-6-methoxy-2-pyridinecarboxylate 
• 308357-96-2 n-propyl 4-(hydroxymethyl)-6-methoxy-2-pyridinecarboxylate 
• 193001-91-1 2-chloro-4-hydroxymethyl-6-methoxypyridine 
• 5398-44-7 2,6-dichloropyridine-4-carboxylic acid 
• 99-11-6 citrazinic acid 

Downstream Products

• 308357-98-4 (+)-methyl N-(benzyloxycarbonyl)-3-(n-propyloxycarbonyl-6-methoxy-4-pyridinyl)-L-alaninate 
• 478946-88-2 4-((S)-2-Benzyloxycarbonylamino-2-carboxy-ethyl)-6-methoxy-pyridine-2-carboxylic acid 

Relevant academic research and scientific papers

Nonproteinogenic amino acids: An efficient asymmetric synthesis of (S)-(-)-acromelobic acid and (S)-(-)-acromelobinic acid

An efficient synthesis of (S)-(-)-acromelobic acid (1) and (S)-(-)-acromelobinic acid (2) is described via asymmetric hydrogenation protocol. Asymmetric hydrogenation of dehydroamino acid derivative 23 using (R,R)-[Rh(DIPAMP)(COD)]BF4 catalyst followed by removal of the protective groups afforded (S)-(-)-acromelobic acid (1) in >98% ee. The key intermediate 23 was prepared from citrazinic acid (8). The dehydroamino acid derivative 33 required for the synthesis of (S)-(-)-2 was prepared from 2,5-lutidine (27), which upon hydrogenation using (S,S)-[Rh(Et-DuPHOS)(COD)]BF4 catalyst afforded (S)-(+)-34 in 93% yield and >96% ee. Removal of protective groups in (S)-(+)-34 afforded (S)-(-)-acromelobinic acid (2) in good overall yield.

An efficient enantioselective synthesis of (S)-(-)-acromelobic acid

(Equation Presented) A highly efficient enantioselective synthesis of (S)-(-)-acromelobic acid (1) was achieved via asymmetric hydrogenation of dehydroamino acid derivative (3) using (R,R)-[Rh(DIPAMP)(COD)]BF4 catalyst followed by removal of protective groups in >98% ee and good over all yield. The key intermediate (3) was prepared from the commercially available citrazinic acid (4) in six steps.