A Facile Synthesis of N-substituted D-arabino-piperidinol Phosphates from the Inositol Phosphate α-Trinositol

Synlett

Volumn 1996, Issue 4, 1996, Pages 361-362

  Malmberg, Mats ^a   Rehnberg, Nicola ^b  

^a Ideon Science Park   (Sweden)

^b Perstorp Pharma ^*  (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0010460024     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5406     Document Type: Article

References (23)

1. Sirén, M. EPO 179440, 1990.
2. (a) Claxon, A.; Morris, C.; Blake, D.; Sirén, M.; Halliwell, B.; Gustafsson, T.; Lövkvist, B.; Bergelin, I. Agents Actions 1990, 29, 68.
3. (b) Wahlestedt, C.; Reis, D. J.; Yoo, H.; Adamsson, M.; Andersson, D.; Edvinsson, L. Neurosci. Lett. 1992, 143, 123.
4. (c) Lund, T.; Reed, R. J. Trauma 1994, 36, 761.
5. (a) Fellows, L. E. and Nash, R. J. Sci. Progress 1990 74, 245.
6. (b) Fellows, L. E. Chem. Britain 1987, 842.
7. For the decomposition of iodate with formation of oxygen, see Greenwood and Earnshaw, Chemistry of the Elements, Pergamon press, 1989, 1011.
8. (a) Theander, O. Adv. Carbohydr. Chem. 1962, 17, 223.
9. (b) Guthrie, R. D. Adv. Carbohydr. Chem 1961, 16, 105.
10. Not optimized.
11. It is assumed that an excess of the amine is required to assure reasonable concentration of unprotonated amine and to compensate for some oxidation that may take place as is indicated by a varying degree of coloration.
12. For the preparation of 4-(benzyloxycarbonylamino)butylamine see Atwell, G. J. and Denny, W. A. Synthesis 1984, 1032.
13. Dionex AS11 column eluted with a linear gradient of sodium hydroxide (6 → 77 mM NaOH), detection by conductivity.
14. 31P-NMR 1.8, 1.7, 1.6.
15. 31P-NMR spectra were recorded on Varian Unity 300 by Reserca AB, Stockholm, Sweden.
16. -1; Anal. Found: P,16.9.
17. -1; Anal. Found: P, 16.5.
18. The crude product (1 mmol) was purified by anion-exchange chromatography (Dowex 1-X8, 200-400 mesh, 1 x 100 cm) with a linear gradient of hydrochloric acid (0 → 0.3 M, 100 ml/h). Calcium hydroxide was added to fractions containing product and the precipitated calcium salt was collected and treated with an excess of an acidic resin (Dowex 50W-X8, 100-200 mesh). The acidic solution was neutralised with sodium hydroxide and the final product was obtained as an amorphous solid after freeze drying. See also Goldschmidt, B. Carbohydr. Res. 1990, 208, 105.
19. -1; Anal. Found: P, 12.0.
20. -1; Anal. Found: P, 11.1.
21. Screening included Carrageenan-induced Edema (Winter, C. A.; Risley, G. A.; and Nuss, G. W. Proc. Soc. Exp. Biol. Med., 1962, 111, 544) Acetic Acid-Induced Writhing (Collier, H. O. J.; Dinneen, L. C.; Johnson, C. A.; Schneider C. Br. J. Pha. Chemother., 1968, 32, 294), and Shock Sensitivity (Charpentier, J. C. R. Soc. Biol., 1961, 155, 727) tests in mice, ITEM-labo, Le Genest-St-Isle, France.
22. Screening included Carrageenan-induced Edema (Winter, C. A.; Risley, G. A.; and Nuss, G. W. Proc. Soc. Exp. Biol. Med., 1962, 111, 544) Acetic Acid-Induced Writhing (Collier, H. O. J.; Dinneen, L. C.; Johnson, C. A.; Schneider C. Br. J. Pha. Chemother., 1968, 32, 294), and Shock Sensitivity (Charpentier, J. C. R. Soc. Biol., 1961, 155, 727) tests in mice, ITEM-labo, Le Genest-St-Isle, France.
23. Screening included Carrageenan-induced Edema (Winter, C. A.; Risley, G. A.; and Nuss, G. W. Proc. Soc. Exp. Biol. Med., 1962, 111, 544) Acetic Acid-Induced Writhing (Collier, H. O. J.; Dinneen, L. C.; Johnson, C. A.; Schneider C. Br. J. Pha. Chemother., 1968, 32, 294), and Shock Sensitivity (Charpentier, J. C. R. Soc. Biol., 1961, 155, 727) tests in mice, ITEM-labo, Le Genest-St-Isle, France.