Stereoselective syntheses of heptaprenylphosphoryl β-d-arabino-and β-d-ribo-furanoses

Tetrahedron Letters

Volumn 50, Issue 19, 2009, Pages 2242-2244

  Liav, Avraham ^a   Ciepichal, Ewa ^b   Swiezewska, Ewa ^b   Bobovská, Adela ^c   Dianišková, Petronela ^c   Blaško, Jaroslav ^c   Mikušová, Katarína ^c   Brennan, Patrick J ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

^b INSTITUTE OF BIOCHEMISTRY AND BIOPHYSICS   (Poland)

^c Physics and Informatics   (Slovakia)

Author keywords

DPA; Heptaprenylphosphoryl d arabinofuranose; Heptaprenylphosphoryl d ribofuranose; Mycobacteria

Indexed keywords

EPIMERASE; FURANONE DERIVATIVE; HEPTAPRENYLPHOSPHORYL BETA ARABINOFURANOSE; HEPTAPRENYLPHOSPHORYL BETA RIBOFURANOSE; PHOSPHORAMIDOUS ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

CORYNEBACTERINEAE;

EID: 62749141936     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.02.188     Document Type: Article

References (17)

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9. Liav A., Swiezewska E., Ciepichal E., and Brennan P.J. Tetrahedron Lett. 47 (2006) 8781-8783
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11. Ye X.Y., Lo M.C., Brunner L., Walker D., Kahne D., and Walker S. J. Am. Chem. Soc. 123 (2001) 3155-3156
12. 10 (40 mg). DMF (0.2 mL) was added, and the mixture was stirred at 70 °C for 4 h. The mixture was dried and the residue was chromatographed on silica gel (60 Å, 70-230 mesh). Elution with methylene chloride-methanol 5:1 (containing 0.5% of concentrated ammonium hydroxide solution) removed fast moving byproducts. Continued elution with the same solvent system gave the tri-O-TBDMS derivative of 1 (5). This product was then treated with ammonium fluoride (90 mg) and 15% methanolic ammonium hydroxide solution (2 mL) in methanol (4 mL) at 65 °C for 14 h. The mixture was cooled and diluted with methylene chloride, and the insoluble material was filtered off and washed with methylene chloride-methanol 5:1. The filtrate was dried and the residue was chromatographed on silica gel. The product was eluted with methylene chloride-methanol-ammonium hydroxide 65:125:4 (12 mg, 53%).
13. 3OD): δ 5.47 (t, J = 4.6 Hz, 1H, H-1), 5.42 (t, J = 6.4 Hz, 1H), 5.13-5.07 (m, 4 H), 4.43 (t, 6.8 Hz, 2H), 4.06 (t, J = 7.6 Hz, 1H), 3.98 (m, 1H), 3.80-3.72 (m, 1H), 3.64 (dd, J = 5.0, 12.0 Hz, 1H), 2.14-1.94 (m, 20H), 1.74 (s, 3H), 1.68 (s, 9H), 1.64 (s, 3H), 1.61 (s, 3H), 1.60 (s, 6H), 1.34-1.26 (m, 6H). Mass spectrometry (negative ion-electrospray mode): 705.452 (M-1).
14. 10 in dichloromethane (0.3 mL) were added. The mixture was then stirred at room temperature for 4 h. The mixture was dried and the residue was triturated with petroleum ether (3 × 3 mL). The organic solution was dried and the residue was dissolved in tetrahydrofuran (1.5 mL). Hydrogen peroxide solution (35%, 20 μL) was added and the mixture was stirred at room temperature for 30 s. It was then treated with methanolic potassium hydroxide solution (5%, 6 mL) at room temperature for 30 min. The mixture was partitioned between water (10 mL) and dichloromethane (10 mL). The organic phase was washed with a saturated sodium chloride solution and dried under vacuum. The residue was chromatographed on silica gel (60 Å, 70-230 mesh). Elution with dichloromethane-methanol 5:1 (containing concentrated ammonium hydroxide solution, 1% v/v) removed at first fast moving impurities. Continued elution with the same solvent system gave the pure product. Yield: 19 mg (46%). Finally, the product was deprotected by treatment with ammonium fluoride (150 mg) in methanolic ammonium hydroxide solution (5%, 9 mL) at 67 °C for 17 h. The mixture was cooled and diluted with dichloromethane. The insoluble crystalline material was filtered off and washed with dichloromethane-methanol 4:1. The filtrate was dried and the residue was chromatographed on silica gel. Elution with dichloromethane-methanol-ammonium hydroxide 65:25:4 removed fast moving byproducts. Continued elution with the same solvent system, followed by dichloromethane-methanol-ammonium hydroxide 65:125:4 gave the ribo-analog 2. Yield: 7.5 mg (78%).
15. 3OD): δ 5.48 (d, J = 4.8 Hz, 1H, H-1), 5.42 (t, J = 6.8 Hz, 1H), 5.16-5.09 (m, 4 H), 4.41 (t, J = 6.6 Hz, 2H), 4.30 (dd, J = 4.4, 7.3 Hz, 1H), 3.99 (d, J = 4.4 Hz, 1H), 3.98-3.95 (m, 1H), 3.82 (dd, J = 2.9, 12.2 Hz, 1H), 3.63 9dd, J = 5.37, 12.2 Hz 1H), 2.14-1.97 (m, 20H), 1.76 (s, 3H), 1.70 (s, 9H), 1.69 (s, 3H), 1.63 (s, 3H), 1.61 (s, 6H), 1.37-1.31 (m, 6H). Mass spectrometry (negative ion-electrospray mode): 705.448 (M-1).
16. 17
17. Besra G.S. In: Parish T., and Stoker N.G. (Eds). Methods in Molecular Biology. Mycobacteria Protocols Vol. 101 (1998), Humana Press 91-107