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Бредихина, З. А.; Savel'ev, D. V.; Бредихин, А. А.

doi:10.1023/a:1015561532507

Cited by 23 publications

(8 citation statements)

References 12 publications

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“…(4R,5R)-4-Hydroxymethyl-5-(4-nitrophenyl)oxazolidin-2-one (8). A mixture of 7 and 8 was isolated from the mother liquor obtained in the previous experiment (3.27 g, 33%).…”

Section: 'R4r)-4-[hydroxy(4-nitrophenyl)methyl]oxazolidin-2-one (7)mentioning

confidence: 99%

“…It is known that the closure of the oxazolidinone ring upon treatment of a suitable methylcarbamate proceeds rather rapidly even at room temperature and in a slightly basic medium (pH 9.5) in only 20 min [8]. But we maintained the reaction mixture under similar conditions for about 120 h, and only a slight amount of oxazolidinone 4 was obtained as a precipitate [9].…”

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confidence: 96%

“…These compounds display a variety of biological activity [1][2][3][4] and are used in asymmetric synthesis [5]. Formation of the 2-oxazolidinone ring is used when necessary to protect both the adjacent amino and hydroxy groups [6][7][8].In our previous work [9], we synthesized (1S,2S)-2-ethoxycarbonylamino-1-(4-nitrophenyl)-1,3-propanediol (2) from (1S,2S)-2-amino-1-(4-nitrophenyl)-1,3-propanediole (1) with subsequent conversion to isomeric 2-oxazolidinones: (1'S,4S)-4-[hydroxy(4-nitrophenyl)methyl)oxazolidin-2-one (4) and (4S,5S)-4-hydroxymethyl-5-(4-nitrophenyl)oxazolidin-2-one (3) according to Scheme 1.It is known that the closure of the oxazolidinone ring upon treatment of a suitable methylcarbamate proceeds rather rapidly even at room temperature and in a slightly basic medium (pH 9.5) in only 20 min [8]. But we maintained the reaction mixture under similar conditions for about 120 h, and only a slight amount of oxazolidinone 4 was obtained as a precipitate [9].…”

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confidence: 99%

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confidence: 99%

“…In light of the data on the reactivity of propanediol 2, (1R,2R)-2-ethoxycarbonylamino-1-(4-nitrophenyl)-1,3-propanediol (6) was converted to (1'R,4R)-4-[hydroxy(4-nitrophenyl)methyl]oxazolidin-2-one (7) and (4R,5R)-4-hydroxymethyl-5-(4-nitrophenyl)oxazolidin-2-one (8). Stereoisomers display different biological activity and, thus, hold interest for biological testing.…”

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confidence: 99%

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Synthesis of isomeric 2-oxazolidinones from (1R,2R)-and (1S,2S)-2-amino-1-(4-nitrophenyl)-1,3-propanediols

Madesclaire

Zaitsev

Zaitseva

et al. 2007

Chem Heterocycl Comp

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Keywords: (1R,2R)-and (1S,2S)-2-amino-1-(4-nitrophenyl)-1,3-propanediols, (4R,5R)-and (4S,5S)-4-hydroxymethyl-5-(4-nitrophenyl)oxazolidin-2-ones, (1'R,4R)-and (1'S,4S)-4-[hydroxy(4-nitrophenyl)-methyl]oxazolidin-2-ones.2-Oxazolidinones have attracted considerable attention in chemistry. These compounds display a variety of biological activity [1][2][3][4] and are used in asymmetric synthesis [5]. Formation of the 2-oxazolidinone ring is used when necessary to protect both the adjacent amino and hydroxy groups [6][7][8].In our previous work [9], we synthesized (1S,2S)-2-ethoxycarbonylamino-1-(4-nitrophenyl)-1,3-propanediol (2) from (1S,2S)-2-amino-1-(4-nitrophenyl)-1,3-propanediole (1) with subsequent conversion to isomeric 2-oxazolidinones: (1'S,4S)-4-[hydroxy(4-nitrophenyl)methyl)oxazolidin-2-one (4) and (4S,5S)-4-hydroxymethyl-5-(4-nitrophenyl)oxazolidin-2-one (3) according to Scheme 1.It is known that the closure of the oxazolidinone ring upon treatment of a suitable methylcarbamate proceeds rather rapidly even at room temperature and in a slightly basic medium (pH 9.5) in only 20 min [8]. But we maintained the reaction mixture under similar conditions for about 120 h, and only a slight amount of oxazolidinone 4 was obtained as a precipitate [9].In this conection the aim of the present work was the search of the conditions most favorable for formation of the one of the isomeric 2-oxazolidinones, permitting a reduction of the reaction time.Base is a catalyst in the formation of 2-oxazolidinones but it may lead to undesired racemization. Propanediol 2 is sensitive to the pH value and the solution at pH > 10 turns reddish; the product isolated is less pure. Thus, propanediol 2 is initially [9] treated with a 1:1 mixture of water and saturated methanolic potassium carbonate, which has pH ~9.5.In a search for optimal reaction conditions, the pH of the reaction solution was raised to 10 by addition solid potassium hydroxide. Furthermore, different amounts of propanediol 2 were treated with equal volumes of the indicated solution. In experiment 5, 20 ml water was added to 50 ml used solution to reduce the solubility of oxazolidinone 4 (Table 1).

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“…(4R,5R)-4-Hydroxymethyl-5-(4-nitrophenyl)oxazolidin-2-one (8). A mixture of 7 and 8 was isolated from the mother liquor obtained in the previous experiment (3.27 g, 33%).…”

Section: 'R4r)-4-[hydroxy(4-nitrophenyl)methyl]oxazolidin-2-one (7)mentioning

confidence: 99%

mentioning

confidence: 96%

mentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

See 3 more Smart Citations

Synthesis of isomeric 2-oxazolidinones from (1R,2R)-and (1S,2S)-2-amino-1-(4-nitrophenyl)-1,3-propanediols

Madesclaire

Zaitsev

Zaitseva

et al. 2007

Chem Heterocycl Comp

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Formation of Alcohols and Phenols by Substitution

Larock

Worlikar

2018

Comprehensive Organic Transformations

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Substrate Engineering and its Synthetic Utility in the Sulfation of Primary Aliphatic Alcohol Groups by a Bacterial Arylsulfotransferase

Hartog

Wever

2015

Adv Synth Catal

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Theu se of substrate engineering allowed the enzymatic sulfation by an arylsulfotransferase from Desulfitobacterium hafniense of an umber of carbohydrate derivatives.S pecific sulfation of carbohydratesc hemicallyo re nzymatically is notoriously difficult or complex. As we have shown previously,the arylsulfotransferase is able to sulfate avariety of phenolic alcoholsa sw ella sn on-phenolic alcohols,a lbeit the conversion in the latter case is limited and in general less than af ew percent. Here we used the strategyo fs ubstrate engineering to increase the conversion by attaching ah ydrophobic group to the carbohydrate.T he formed sulfated intermediates mayb eu sed as building blocks in the formation of more complexs ulfated carbohydrates via at ransglycosylation reaction.

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Cited by 23 publications

References 12 publications

Synthesis of isomeric 2-oxazolidinones from (1R,2R)-and (1S,2S)-2-amino-1-(4-nitrophenyl)-1,3-propanediols

Synthesis of isomeric 2-oxazolidinones from (1R,2R)-and (1S,2S)-2-amino-1-(4-nitrophenyl)-1,3-propanediols

Formation of Alcohols and Phenols by Substitution

Substrate Engineering and its Synthetic Utility in the Sulfation of Primary Aliphatic Alcohol Groups by a Bacterial Arylsulfotransferase

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