A CONVENIENT SYNTHESIS OF DL-GLUTAMIC ACID FROM β-PROPIOLACTONE

1956 ◽  
Vol 34 (10) ◽  
pp. 1440-1443 ◽  
Author(s):  
Guy Talbot ◽  
Roger Gaudry ◽  
Louis Berlinguet
Keyword(s):  
Glutamic Acid ◽  
Acid Hydrolysis ◽  
Sodium Salt ◽  
Intermediate Product ◽  
Diethyl Ester ◽  
New Synthesis ◽  
Convenient Synthesis

A new synthesis of DL-glutamic acid was carried out in an over-all yield of 87% from condensation between β-propiolactone and the sodium salt of diethyl acetamidomalonate, followed by acid hydrolysis. When desired, the intermediate product, the diethyl ester of N-acetyl-2-carbethoxyglutamic acid, could be isolated in a 68% yield and hydrolyzed to glutamic acid via the hydrochloride in a 95% yield.

scholarly journals A NEW SYNTHESIS OF DL-γ-HYDROXY-ORNITHINE

1956 ◽  
Vol 34 (7) ◽  
pp. 911-914 ◽  
Author(s):  
Guy Talbot ◽  
Roger Gaudry ◽  
Louis Berlinguet
Keyword(s):  
Acid Hydrolysis ◽  
Allyl Chloride ◽  
Quantitative Yield ◽  
Dimethyl Formamide ◽  
New Synthesis ◽  
Convenient Synthesis

A convenient synthesis of DL-hydroxy-ornithine is described. Starting from diethyl allylmalonate, it involves treatment with sulphuryl chloride followed by hydrolysis and distillation to give a 90% yield of 2,5-dichloro-4-valerolactone. Condensation of this with two equivalents of potassium phthalimide in dimethyl-formamide gives a quantitative yield of crude 2,5-diphthalimido-4-valerolactone. This lactone is converted quantitatively by acid hydrolysis to DL-γ-hydroxyornithine, isolated as the dihydrochloride of the corresponding 2,5-diamino-4-valerolactone. The over-all yield calculated from allyl chloride is 80%.

scholarly journals A NEW SYNTHESIS OF GLUTAMIC ACID

1931 ◽  
Vol 94 (2) ◽  
pp. 599-609
Author(s):  
Max S. Dunn ◽  
B.W. Smart ◽  
C.E. Redemann ◽  
K.E. Brown
Keyword(s):  
Glutamic Acid ◽  
New Synthesis

Synthesis of 5'-O-phosphonomethyl derivatives of pyrimidine 2'-deoxynucleosides

1990 ◽  
Vol 55 (10) ◽  
pp. 2521-2536 ◽  
Author(s):  
Marcela Krečmerová ◽  
Hubert Hřebabecký ◽  
Antonín Holý
Keyword(s):  
Sodium Salt ◽  
Catalytic Hydrogenation ◽  
Bond Cleavage ◽  
Diethyl Ester ◽  
Derivatives Of

Reaction of sodium salt of 3-N,3'-O-bis(benzyloxymethyl)-2'-deoxyuridine (X) and 3-N,3'-O-bis(benzyloxymethyl)-2'-deoxythymidine (XI) with diethyl p-toluenesulfonyloxymethanephosphonate in dimethylformamide afforded diesters of the respective 5'-O-phosphonomethyl derivatives XII and XVII. Diethyl esters of 5'-O-phosphonomethyl-2'-deoxynucleosides XV and XIX, obtained after hydrogenolytic removal of the benzyloxymethyl groups, were converted into free 2'-deoxy-5'-O-phosphonomethyluridine (XVI) and a mixture of anomeric 1-(2-deoxy-5-O-phosphonomethyl-β-D-erythro-pentofuranosyl)thymines (XXIIIa, XXIIIb), respectively. Analogously, 2'-deoxy-5'-O-phosphonomethylcytidine (XXXIV) was prepared from 4-N-benzoyl-2'-deoxy-3'-O-(tetrahydro-2H-pyran-2-yl) cytidine (XXX) via diethyl ester of 2'-deoxy-5'-O-phosphonomethylcytidine (XXXIII). This compound reacted with bromotrimethylsilane to give compound XXXIV without anomerization and nucleoside bond cleavage. Condensation of the protected nucleosides X and XI with dibenzyl p-toluenesulfonyloxymethanephosphonate afforded dibenzyl esters of the corresponding 5'-O-phosphonomethyl derivatives XIII and XVIII. The free 5'-O-phosphonomethyl derivatives XVI and XXIIIa were obtained from XIII and XVIII by catalytic hydrogenation.

A New Synthesis of Fluorescein Isothiocyanate Labeled Poly(styrenesulfonate sodium salt)

2004 ◽  
Vol 37 (12) ◽  
pp. 4731-4735 ◽  
Author(s):  
Rongjuan Cong ◽  
Sibel Turksen ◽  
Paul Russo
Keyword(s):  
Sodium Salt ◽  
Fluorescein Isothiocyanate ◽  
New Synthesis
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