An Efficient Synthesis of Enantiomeric (S)-Phosphocarnitine

Wróblewski, Andrzej E.; Hałajewska-Wosik, Anetta

doi:10.1002/1099-0690(200208)2002:16<2758::aid-ejoc2758>3.0.co;2-q

Cited by 25 publications

(16 citation statements)

References 19 publications

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“…The other argument supporting the H-bonding in (2S,3S)-13 comes from the close resemblance of the H-bonded fragment in (2S,3S)-13 with that in a 2-hydroxyalkyl phosphonate system 14, since the stabilising role of the intramolecular hydrogen bond in 2-hydroxyalkyl phosphonates has been well recognised. [49][50][51][52] This clearly demonstrates that the OH and P@O groups are located on the same side of the 1,2-oxaphospholane ring and thus proves the (S)-absolute configuration at the phosphorus in (2S,3S)-13. 31 …”

Section: Resultsmentioning

confidence: 99%

Stereochemistry of cycloaddition of (S)-N-(1-phenylethyl)-C-diethoxyphosphorylated nitrone with vinyl acetate. Studies on mutarotation of 3-(O,O-diethylphosphoryl)-5-hydroxyisoxazolidines

Piotrowska

2008

Tetrahedron: Asymmetry

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Section: Resultsmentioning

confidence: 99%

Stereochemistry of cycloaddition of (S)-N-(1-phenylethyl)-C-diethoxyphosphorylated nitrone with vinyl acetate. Studies on mutarotation of 3-(O,O-diethylphosphoryl)-5-hydroxyisoxazolidines

Piotrowska

2008

Tetrahedron: Asymmetry

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“…5). This is commonly observed for β-hydroxyphosphonates [35]. This conclusion is further supported by the lack of the vicinal phosphorus-HC2 coupling as expected for the gauche relationship within a H-C2-C1-P unit [31,32].…”

Section: Conformational Analysismentioning

confidence: 52%

Acyclic nucleoside phosphonates containing the amide bond: hydroxy derivatives

et al. 2019

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To study the influence of a linker rigidity and changes in donor-acceptor properties, three series of nucleotide analogs containing a P-X-HN-C(O)-residue (X=CH(OH)CH 2 , CH(OH)CH 2 CH 2 , CH 2 CH(OH)CH 2 ) as a replacement for the P-CH 2 -O-CHR-fragment in acyclic nucleoside phosphonates, e.g., adefovir, cidofovir, were synthesized. EDC proved to provide good yields of the analogs from the respective ω-amino-1-or -2-hydroxyalkylphosphonates and nucleobase-derived acetic acids. New phosphorus-nucleobase linkers are characterized by two fragments of the restricted rotation within amide bonds and in four-atom units (P-CH(OH)-CH 2 -N, P-CH(OH)-CH 2 -C and P-CH 2 -CH(OH)-C) in which antiperiplanar disposition of P and N/C atoms was deduced from 1 H and 13 C NMR spectral data. The synthesized analogs P-X-HNC(O)-CH 2 B [X=CH(OH)CH 2 , CH(OH)CH 2 CH 2 , CH 2 CH(OH)CH 2 ] appeared inactive in antiviral assays on a wide variety of DNA and RNA viruses at concentrations up to 100 μM, while two phosphonates showed cytostatic activity towards myeloid leukemia (K-562) and multiple myeloma cells (MM.1S) with IC 50 of 28.8 and 40.7 μM, respectively. Graphical abstract 586 cm −1 ; 1 H NMR (600 MHz, CD 3 OD): δ = 8.01 (s, 1H, HC = CBr), 4.45 (s, 2H, C(O)CH 2 ), 4.23-4.16 (m, 4H, 2 × POCH 2 CH 3 ,), 3.96 (ddd, J H1-H2b = 10.7 Hz, J H1-P = 7.4 Hz, J H1-H2a = 3.1 Hz, 1H, PCH) 3.48 (ddd, J H3a-H3b = 13.5 Hz, J H3a-H2a = 8.2 Hz, J H2a-P = 7.0 Hz, 1H, PCCC H a H b ), 3.41 (ddd, J H3a-H3b = 13.5 Hz, J H3b-H2a = 7.3 Hz, J H3b-H2b = 4.9 Hz, 1H, PCCCH a H b ), 1.99 (ddddd, J H2a-H2b = 14.0 Hz, J H2a-H3a = 8.2 Hz, J H2a-H3b = 7.3 Hz, J H2a-P = 6.7 Hz, J H2a-H1 = 3.1 Hz, 1H, PCCH a H b ), 1.86 (ddddd, J H2a-H2b = 14.0 Hz, J H2b-H1 = 10.7 Hz, J H2b-P = 9.5 Hz, J H2b-H3a = 7.0 Hz, J H2b-H3b = 4.9 Hz, 1H, PCCH a H b ) 1.36 (t, J = 7.1 Hz, 6H, 2 × POCH 2 CH 3 ) ppm; 13 C NMR (151 MHz, CD 3 OD): δ = 167.95, 160.77, 150.89, 145.86, 95.13, 64.35 (d, J = 167.4 Hz, PC), 62.90 and 62.56 (2 × d, J = 7.1 Hz, 2 × POC), 49.99, 35.68 (d, J = 16.1 Hz, PCCC), 30.78 (d, J = 3.0 Hz, PCC), 15.42 and 15.38 (2 × d, CH a H b ), 4.31-4.14 (m, 4H, 2 × POCH 2 CH 3 ), 4.08 (ddd, J H1-H2b = 9.2 Hz, J H1-P = 8.2 Hz, J H1-H2a = 3.6 Hz, 1H, PCHCH 2 ), 3.73 (ddd, J H2a-H2b = 14.0 Hz, J H2a-P = 7.2 Hz, J H2a-H1 = 3.6 Hz, 1H, PCCH a H b ), 3.38 (ddd ~ dt, J H2b-H2a = 14.0 Hz, J H2b-H1 = 9.2 Hz, J H2b-P = 8.5 Hz, 1H, PCCH a H b ), 1.92 (d, J = 1.1 Hz, 3H, HC = CCH 3 ), 1.39 (t, J = 7.0 Hz, 6H, 2 × POCH 2 CH 3 ) ppm; 13 C NMR (151 MHz, CD 3 OD): δ = 168. 45, 165.54, 151.72, 142.17, 109.78, 65.84 (d, J = 164.3 Hz, PC), 63.04 and 62.73 (2 × d, J = 6.9 Hz, 2 × POC), 49.56, 41.11 (d, J = 8.6 Hz, PCC), 15.40 and 15.36 (2 × d, J = 5.1 Hz, 2 × POCC), 10.78 ppm; 31 P NMR (81 MHz, CD 3 OD): δ = 23.74 ppm. [2-(3,4-dihydro-5-methyl-2,4-dioxopyrimidin-1(2H)-yl)acetamido]-1-hydroxypropylphosphonate (8d, C 14 H 24 N 3 O 7 P) According to the general procedure from 0.180 g diethyl 3-amino-1-hydroxypropylphosphonate (11, 0.852 mmol) and 0.157 g (thymine-1-yl)acetic acid (13d, 0.852 mmol), th...

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“…The dimenthyl esters were hydrolysed to free hydroxyphosphonic acids whose configuration was determined earlier. [25][26][27][28][29][30][31][32] For example, the hydrolysis of dimenthyl 2-hydroxy-3-chloropropylphosphonate 4b with conc. hydrochloric acid in dioxane afforded the enantiopure (S)-2-Hydroxy-3-chloropropylphosphonic acid (S)-6b with high yield.…”

Section: Methodsmentioning

confidence: 65%

Enantioselective reduction of ketophosphonates using adducts of chiral natural acids with sodium borohydride

Gryshkun¹,

Nesterov²,

Kolodyazhnyi³

2012

Arkivoc

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Dedicated to Prof. Paweł Kafarski to honor the achievements within his career AbstractA method for asymmetric reduction of α-and β ketophosphonates using chiral complexes prepared from sodium borohydride and natural aminoacids or tartaric acids was developed. Reduction of α or β ketophosphonates by these reagents led to formation of chiral (S)-or (R)-hydroxyphosphonates. Reduction of chiral di-(1R,2S,5R)-menthylketophosphonates by the chiral complexes NaBH 4 /(R,R)-proline or NaBH 4 /(R,R)-tartaric acid due to the double matched asymmetric induction resulted in increased stereoselectivity of the reaction and led to the formation of hydroxyphosphonates up to 90% ee or higher. Dimenthyl 2-hydroxy-3-chloropropylphosphonate was utilized as a chiron for the preparation of a number of biologically active compounds in multigram quantity.

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An Efficient Synthesis of Enantiomeric (S)-Phosphocarnitine

Cited by 25 publications

References 19 publications

Stereochemistry of cycloaddition of (S)-N-(1-phenylethyl)-C-diethoxyphosphorylated nitrone with vinyl acetate. Studies on mutarotation of 3-(O,O-diethylphosphoryl)-5-hydroxyisoxazolidines

Stereochemistry of cycloaddition of (S)-N-(1-phenylethyl)-C-diethoxyphosphorylated nitrone with vinyl acetate. Studies on mutarotation of 3-(O,O-diethylphosphoryl)-5-hydroxyisoxazolidines

Acyclic nucleoside phosphonates containing the amide bond: hydroxy derivatives

Enantioselective reduction of ketophosphonates using adducts of chiral natural acids with sodium borohydride

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