81546-71-6

Upstream product

• 76338-91-5 2-<(benzyloxycarbonyl)amino>-4-bromobutanoic acid methyl ester 
• 81546-70-5 methyl N^α-benzyloxycarbonylamino-γ-iodobutyrate 
• 75-52-5 nitromethane 
• 21149-17-7 methyl 2-(benzyloxycarbonylamino)acrylate 

Downstream Products

• 114195-60-7 dimethyl ((benzyloxy)carbonyl)aspartate 
• 245368-86-9 2-amino-4-nitro-butyric acid methyl ester 
• 245368-87-0 2-{4-[(2-acetylamino-4-oxo-3,4,5,6,7,8-hexahydro-pyrido[2,3-d]pyrimidin-6-ylmethyl)-formyl-amino]-benzoylamino}-4-nitro-butyric acid methyl ester 
• 245368-88-1 2-[N-[4-[N-[(2-acetamido-4(3H)oxopyrido[2,3-d]pyrimidin-6-yl)methyl]formamido]benzoyl]amino]-4-nitrobutanoic acid methyl ester 
• 96921-58-3 methyl 2-[(benzyloxycarbonyl)amino]-4-oxobutanoate 
• 31332-88-4 (S)-3-(N-benzyloxycarbonylamino)tetrahydrofuran-2-one 
• 81546-73-8 dicyclohexylammonium N^α-benzyloxycarbonylamino-γ-nitrobutyrate 

Relevant academic research and scientific papers

Synthesis of the γ-sulfinic acid and γ-nitro analogues of 5- deazatetrahydrofolic acid

Analogues of 5-deaza-5,6,7,8-tetrahydrofolic acid with a γ-sulfinic acid group or γ-nitro group in place of the γ-carboxyl group of the glutamate side chain were synthesized as diastereomeric mixtures, and were tested for their ability to inhibit the grow

Convenient route to γ-nitro-α-amino acids: Conjugate addition of nitroalkanes to dehydroalanine derivatives

γ-Nitro-α-amino acid derivatives are obtained in good yield from the base-catalysed conjugate addition of nitroalkanes to N-protected dehydroalanine esters (methyl 2-amidoacrylates). The outcome of the reaction is dependent on the N-protecting group (the ease of the product formation correlates with the electron-withdrawing ability and hence stabilising effect on the adduct α-anion of the 2-substituent in the order phthalimido > benzyloxycarbonylamino > acetamido), the nitroalkane, and on the reaction conditions. Conditions were established in reactions of methyl 2-phthalimidoacrylate 4 with nitromethane for selectively obtaining 1 : 1-, 2 : 1- or 3 : 1-adducts. Good yields of the 1 : 1-adducts are obtained when the reaction is carried out with an excess of nitroalkane. Restricting the amount of nitromethane gives rise to the higher adducts. Similarly, reactions of 4 with nitroethane can be adjusted to give 1 : 1- or 2 : 1-adducts selectively. These reactions occur with little or no diastereoselectivity. As a model for a dehydroalanine residue in a peptide chain, the diamide N-cyclohexyl-2-acetamidoacrylamide 7 has been prepared. This dehydroalanine reacts with 2-nitropropane and with nitromethane in refluxing tert-butyl alcohol to give reasonable yields of 1 : 1-adducts. As the nitro group of the resultant γ-nitro-α-amino acid derivatives can be transformed into a variety of other functionalities, the methodology described in this paper offers a versatile entry to a range of γ-substituted α-amino acids.

SYNTHETIC UTILIZATION OF α-AMINO-γ-BROMOBUTYRIC ACID IN THE PREPARATION OF NON-CODED AMINO ACIDS; IR STUDY OF HOMOSERINE

α-Amino-γ-bromobutyric acid and its derivatives were utilized in the preparation of some non-coded (non-proteinogenic) amino acids and their derivatives.The bromine atom was replaced by hydrogen, hydroxyl, iodine and nitro, amino, and thiocyanato groups.Homolanthionine was prepared by two methods.Homoserine has been shown to exist in three crystalline modifications whose differences in the IR spectra indicate conformational changes.