The synthesis of 1,5-dideoxy-1,5-(alkyl)imino-2-C-methyl-D-glucitols

Tetrahedron Letters

Volumn 37, Issue 9, 1996, Pages 1355-1358

  Khanna, Ish K ^a   Weier, Richard M ^a   Julien, Janet ^a   Mueller, Richard A ^a   Lankin, David C ^a   Swenton, Lydia ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIOXANE DERIVATIVE; CARBOHYDRATE DERIVATIVE; POLYOL;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029965828     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00021-4     Document Type: Article

References (19)

1. a) Fleet, G. W. J.; Karpas, A.; Dwek, R. A.; Fellows, L. E.; Tyms, A. S.; Petursson, S.; Namgoong, S. K.; Ramsden, N. G.; Smith, P. W.; Son, J. C.; Wilson, F.; Witty, D. R.; Jacob, G. S.; Rademacher, T. W. FEBS Letters 1991, 237, 128;
2. b) Elbein, A. D. Crit. Rev. Biochem. 1984, 16, 21.
3. a) Ratner, L.; Heyden, N. V.; Dedera, D. Virology 1991, 181, 180;
4. b) Mitsuya, H.; Yarchoan, R.; Broder, S. Science 1990, 249, 1533.
5. a) Khanna, I. K.; Koszyk, F. J.; Stealey, M. A.; Weier, R. M.; Julien, J.; Mueller, R. A.; Rao S. N.; Swenton, L. J. Carbohydr. Chem. 1995, 14, 843;
6. b) Khanna, I. K.; Mueller, R. A.; Weier, R. M. (Searle) U. S. Pat. 5 258 518 (1993);
7. c) Khanna, I. K.; Mueller, R. A.; Weier, R. M. (Searle) U. S. Pat. 5 350 854 (1994).
8. Getman, D. P.; DeCrescenzo, G. A.; Heintz, R. M. Tetrahedron Lett. 1991, 32, 5691.
9. 6) to 17 gave poor yields of the products .
10. a) Maruoko, K.; Takayuki, I.; Yamamoto, H. J. Am. Chem. Soc. 1985, 107, 4573;
11. b) Maruoko, K.; Araki, Y.; Yamamoto, H. Tetrahedron Lett. 1988, 29, 3101.
12. ax (δ 2.8). The NOESY spectra of 21A showed cross peaks between the axial methyl at C-2 and H-4 (δ 3.6) which were absent in the NOESY spectrum of 21B in which H-4 had shifted downfield to δ 4.1. A detailed account of the NMR investigations will be reported separately.
13. Lipschutz, B. H.; Miller, T. A. Tetrahedron Lett. 1989, 30, 7149.
14. +) further confirmed the structure.
15. Getman, D. P.; DeCrescenzo, G. A.; Heintz, R. M., unpublished results.
16. For mechanism of nuclephilic addition to cyclohexanone systems, see e. g., Ashby, E. C.; Laemmle, J. T. J. Org. Chem 1975, 40, 1469;
17. b) Ashby, E. C.; Yu, S. H.; Roling, P.V. J. Org. Chem 1972, 37, 1469;
18. c) Ashby, E. C.; Laemmle, J. T. Chem Reviews 1975, 75, 522;
19. d) Cieolak, A. S. J. Am. Chem. Soc. 1981, 103, 4540.