500720-04-7

Upstream product

• 6305-38-0 α-amino-γ-butyrolactone hydrobromide 
• 103-80-0 phenylacetyl chloride 

Downstream Products

• 500720-05-8 N-phenylacetamido-DL-homoserine 
• 103-82-2 phenylacetic acid 
• 104347-13-9 (R)-(+)-α-amino-γ-butyrolactone hydrochloride 
• 55154-48-8 (S)-N-(2-oxo-tetrahydrofuran-3-yl)-2-phenylacetamide 
• 500720-21-8 compound S 
• 500720-08-1 methyl α-Phenylacetylamino-γ-Phthalimidooxybutyrate 
• 500720-07-0 methyl N-phenylacetyl-O-methanesulfonyl homoserinate 
• 500720-09-2 methyl 2-Phenylacetylamino-4-Aminooxybutyrate 
• 500720-06-9 N-phenylacetamido-DL-homoserine methyl ester 
• 500720-10-5 4-Phenylacetylamino-[1,2]Oxazinan-3-one 

Relevant academic research and scientific papers

Chemo-enzymatic synthesis of the azasugars 1,4-dideoxyallonojirimycin and 1,4-dideoxymannojirimycin

The enzymatic resolution of the N-phenylacetyl derivative of racemic homoserine lactone with penicillin G acylase immobilized on Eupergit C gave (R)-(+)-α-amino-γ-butyrolactone and (S)-(-)-α-N- phenylacetamido-γ-butyrolactone in high enantiomeric purity (ee >99%) and 46-47% yields for each enantiomer. The enantiomers were converted into azasugars 1,4-dideoxyallonojirimycin and 1,4-dideoxymannojirimycin using Wittig olefination, catalytic ring-closing metathesis (RCM), and stereoselective dihydroxylation with OsO4 in 29% overall yield over 11 high yielding steps. Enzyme inhibition studies showed that 1,4-dideoxyallonojirimycin is a better β-glucosidase inhibitor (IC50 32.4 μM toward β-glucosidase from almonds) and a better β-galactosidase inhibitor (IC50 5.9 mM for β-galactosidase from Aspergillus oryzae) than 1,4-dideoxymannojirimycin (IC50 2.86 mM and 12.5 mM for β-glucosidase and β-galactosidase, respectively).

Method for synthesizing oxazinones

New methods and intermediates are discussed for the stereospecific synthesis of oxazinone compounds.

Cyclic hydroxamates, especially multiply substituted [1,2]oxazinan-3-ones

Routes to putative N-acyl-D-ala-D-ala surrogates, beginning with the conversion of 4-, 5-, and 6-membered lactones into 5-, 6-, and 7-membered cyclic hydroxamates, are reported. The key step of the synthesis is trimethylaluminium-promoted cyclization of an ω-aminooxyester. The 7-membered cyclic hydroxamate crystallizes in a chair conformation. Extension of the reaction sequence to homoserine or homoserine lactone leads to cyclocanaline and N-acylated cyclocanalines. The 4-phenylacetamido derivative of cyclocanaline crystallizes in a boat conformation. The attachment of a 2-carboxypropyl substituent to the ring nitrogen of a 4-acylaminocyclocanaline has been effected, prior to cyclization, by coupling of the acyclic aminooxyester precursor to the triflate of benzyl lactate or, after cyclization, by coupling to tert-butyl α-bromopropionate in the presence of potassium fluoride - alumina, followed by removal of the protecting group in each case. A six-membered homolog of the antibiotic lactivicin has been synthesized by the reaction of 4-phenylacetamidocyclocanaline with benzyl 2-oxoglutarate in the presence of carbodiimide, followed by hydrogenolysis. Starting with methyl 2,4-dibromo-2,4-dideoxy-L-erythronate, which is available in two steps from L-ascorbic acid, these reaction sequences have been applied to the stereospecific synthesis of a D-alanine derivative whose nitrogen atom is enclosed within a 3,4-disubstituted [1,2]oxazinan-3-one.