Synthese und spektroskopische Eigenschaften chiraler 1,3‐Oxazolidine

Evers, R.; Michalik, Manfred

doi:10.1002/prac.19913330503

Cited by 5 publications

(1 citation statement)

References 7 publications

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“…Papers published in recent years reported on the use of (+)-I in the synthesis of p-nitrobenzaldehyde [84], chiral crown-esters [85,86], 2-dimethylamino-l-(4-nitrophenyl)-1,3-propanediol [87], homochiral 2-amino-l-aryl-3-halogeno-1-propanols [88], l-aryl-1-acetoxy-3-halogeno-2phthalimidopropanes [89], norpseudoephedrine [90], and 1,3oxazolidines [91][92][93]. Patented processes include the synthesis of D-threo-2-amino-l-(4-aminophenyl)-l,3-propanediol [94], N-acetylation of I [95], and deacetylation of the N-acetyl derivative of I [96].…”

Section: Amino-l-(4-nitrophenyl)-l3-propanediols In Synthesismentioning

confidence: 99%

Levomycetin andthreo-2-amino-1-(4-nitrophenyl)-1,3-propanediol

1998

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Levomycetin, or D-(-)-threo-2-dichloroacetylamino-l-(4-nitrophenyl)-l,3-propanediol, has been used in medicine and veterinary for about 50 years. However, the development of new methods for the synthesis of this drug, the technological perfection of some stages involved in the process, the search for the possibility of using intermediate deacylated derivatives, and quality control of drug preparations are still drawing close attention of researchers. Below we summarize the data published in this field during 1983 -1995. Development of New Methods for the Synthesis of Levomycetin and Perfection of Separate Technological StagesProcesses patented during the past 15 years include acylation of the corresponding aminodiol by dichloroacetic acid methyl ester [1], simultaneous hydroxymethylation and reduction of 2-acetylarnino-2-(4-nitrophenyl)ethan-l-one [2], reduction of 2-acetylarrfino-3-hydroxy-l-(4-nitrophenyl)-1propanone [3,4], and the subsequent deacetylation of the reduced product [5,6], nitriding postponed to the latest stages of the process and nitriding of 5-acetylamino-4-phenyl-1,3dioxane [7], and separation of the enantiomer mixture of the corresponding aminodiols [8]. Of special interest was the study of possible stereochemical inversion of 1S,2S-threo-2amino-2-(4-nitrophenyl)-l,3-propanediol to its IR,1R-enantiomer [9, 10] and the use of asymmetric epoxidation of 3-(4nitrophenyl)-2-propen-1-ol followed by opening of the epoxide cycle [ 11 ]. Also noteworthy is the synthesis and use for investigation purposes of 3H-labeled [12, 13] and 35Cl-labeled [14] levomycetin and its fluorescent derivatives [15,16]. Analytical determination of Levomycetin and the Products of Its MetabolismPapers published during the past 15 years were devoted to determination of levomycetin and its metabolites [17] and 157

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Section: Amino-l-(4-nitrophenyl)-l3-propanediols In Synthesismentioning

confidence: 99%

Levomycetin andthreo-2-amino-1-(4-nitrophenyl)-1,3-propanediol

1998

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ChemInform Abstract: Structure and Reactive Behavior of Activated C=N Double Bonds. Part 12. Synthesis and Spectroscopic Properties of Chiral 1,3‐Oxazolidines.

Evers

Michalik

1992

ChemInform

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Structure and Reactive Behavior of Activated C=N Double Bonds. Part 12.Synthesis and Spectroscopic Properties of Chiral 1,3-Oxazolidines.-The reactions between the diol (II) and dithiocarbimidic esters such as (I) and (IV) proceed with involvement of the secondary or primary alcohol function of (II) to afford oxazolidines such as (III) and (V), respectively. The reaction between (II) and ketenedithioacetals such as (VI) proceeds with involvement of the secondary alcohol function to yield the oxazolidine (VII). The reactions of the enantiomer of (II) proceed analogously. The structures of the chiral oxazolidines (13 representatives) are elucidated by IR and 1H NMR spectroscopy. -(EVERS, R.; MICHALIK, M.; J. Prakt. Chem. 333 (1991) 5, 699-710; Inst. Org. Katalyseforsch. Rostock, O-2500 Rostock 1, Fed. Rep. Ger.; DE)

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Synthesis of (2S,3S)-3-amino-2-phenylthietane

Rozwadowska

1994

Tetrahedron: Asymmetry

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Synthese und spektroskopische Eigenschaften chiraler 1,3‐Oxazolidine

Cited by 5 publications

References 7 publications

Levomycetin andthreo-2-amino-1-(4-nitrophenyl)-1,3-propanediol

Levomycetin andthreo-2-amino-1-(4-nitrophenyl)-1,3-propanediol

ChemInform Abstract: Structure and Reactive Behavior of Activated C=N Double Bonds. Part 12. Synthesis and Spectroscopic Properties of Chiral 1,3‐Oxazolidines.

Synthesis of (2S,3S)-3-amino-2-phenylthietane

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