Stereoselective synthesis of decaprenylphosphoryl β-D-arabinofuranose

Tetrahedron Letters

Volumn 47, Issue 4, 2006, Pages 545-547

  Liav, Avraham ^a   Huang, Hairong ^a   Ciepichal, Ewa ^b   Brennan, Patrick J ^a   McNeil, Michael R ^a  

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

^b INSTITUTE OF BIOCHEMISTRY AND BIOPHYSICS   (Poland)

Author keywords

D Arabinofuranosyl phosphate; DPA; Mycobacteria

Indexed keywords

BACTERIUM LIPOPOLYSACCHARIDE; CARBOHYDRATE DERIVATIVE; DECAPRENYLPHOSPHORYL BETA DEXTRO ARABINOFURANOSE; UNCLASSIFIED DRUG;

ARTICLE; BACTERIAL CELL WALL; CARBOHYDRATE SYNTHESIS; DEPROTECTION REACTION; MYCOBACTERIUM; STEREOCHEMISTRY;

BACTERIA (MICROORGANISMS); CORYNEBACTERINEAE; MYCOBACTERIUM;

EID: 29144492773     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.11.068     Document Type: Article

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12. 11 (27 mg). DMF (0.1 mL) was added, and the mixture was stirred at 67°C for 6 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 product (9 mg, 43%).
13. M.S. Scherman, L. Kalbe-Bournonville, D. Bush, Y. Xin, and M. McNeil J. Biol. Chem. 271 1996 29652 29658
14. The TLC was run in chloroform-methanol-water-M-ammonium acetate-ammonium hydroxide 180:140:23:9:9.
15. D -6.0 (c 0.3, methanol).