478946-91-7

Basic information

• Product Name: 5-((S)-2-Benzyloxycarbonylamino-2-carboxy-ethyl)-6-methoxy-pyridine-2-carboxylic acid
• Synonyms: 5-((S)-2-Benzyloxycarbonylamino-2-carboxy-ethyl)-6-methoxy-pyridine-2-carboxylic acid
• CAS NO: 478946-91-7
• Molecular Weight: 374.35
• Mol File: 478946-91-7.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 5-((S)-2-Benzyloxycarbonylamino-2-carboxy-ethyl)-6-methoxy-pyridine-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5-((S)-2-Benzyloxycarbonylamino-2-carboxy-ethyl)-6-methoxy-pyridine-2-carboxylic acid(478946-91-7)
• EPA Substance Registry System: 5-((S)-2-Benzyloxycarbonylamino-2-carboxy-ethyl)-6-methoxy-pyridine-2-carboxylic acid(478946-91-7)

Safety Data

• Hazardous Substances Data: 478946-91-7(Hazardous Substances Data)

Upstream product

• 401792-84-5 methyl 5-(bromomethyl)-6-methoxy-2-pyridinecarboxylate 
• 401792-87-8 methyl 5-formyl-6-methoxy-2-pyridinecarboxylate 
• 401792-82-3 methyl 6-methoxy-5-methyl-2-pyridinecarboxylate 
• 401792-80-1 methyl 6-hydroxy-5-methyl-2-pyridinecarboxylate 
• 401792-77-6 methyl 5-methyl-2-pyridinecarboxylate N-oxide 
• 29681-38-7 methyl 5-methylpyridine-2-carboxylate 
• 589-93-5 2,5-dimethylpyridine 
• 401792-93-6 (+)-methyl N-(benzyloxycarbonyl)-3-[2-(methoxycarbonyl)-6-methoxy-5-pyridinyl]-L-alaninate 

Relevant articles and documents

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.