A facile synthesis of benzyl 2-amino-3-azido-4-O-p-methoxybenzyl-6-O-benzyl-2,3-dideoxy-α-D- glucopyranoside: A key intermediate in the formation of a didemnin B analog

Journal of Carbohydrate Chemistry

Volumn 15, Issue 3, 1996, Pages 371-381

  Ramanjulu, Joshi M ^a   Joullié, Madeleine M ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0011950795     PISSN: 07328303     EISSN: None     Source Type: Journal    
DOI: 10.1080/07328309608005660     Document Type: Article

References (25)

1. K. L. Rinehart, Jr., J. B. Gloer, J. C. Cook, Jr., S. A. Mizsak, and T. A. Scahill, J. Am. Chem. Soc., 103, 1857 (1981).
2. D. W. Montgomery and C. F. Zukoski, Transplantation , 40, 49 (1985).
3. E. Maldonado, J. A. Lavergne and E. Kraiselburd, P. R. Health Sci. J., 1, 22 (1982).
4. M. B. Hossain, D. Van der Helm, J. Antel, G. M. Sheldrich, S. L. Sanduja, A. J. Weinheimer, Proc. Natl. Acad. Sci. U. S. A., 85, 4118 (1988).
5. H. Kessler, M. Will, J. Antel, H. Beck and G. M. Sheldrick, Helv. Chim. Acta , 72, 530 (1989).
6. M. S. Searle, J. G. Hall, I. Kyratzis and L. P. G. Wakelin, Int. J. Pept. Protein Res., 34, 445 (1989).
7. D. W. Montgomery, D. H. Russell, A. R. Buckley and C. F. Zukoski, Eos Riv. Immunol. Immunofarmacol., 7, 73 (1987).
8. S. C. Mayer, J. Ramanjulu, M. D. Vera, A. Pfizenmayer, and M. M. Joullié, J. Org. Chem., 59, 5192 (1994).
9. K. L. Rinehart and A. M. Lithgow-Bertelloni, Dehydrodidemnin B (PHARMAR) PTC Int, Appl.WO 91 04,985, 18 Apr 1991 1-248086q (GB, 1991).
10. (a) P. H. Gross and R. W. Jeanloz, J. Org. Chem., 32, 2759 (1967);
11. (b) W. M. zu Reckendorf, Methods Carbohydr. Chem., 6, 266 (1972);
12. (c) F. G. De Las Heras, and A. Calvo-Mateo, Carbohydr. Res., 155, 266 (1986);
13. (d) W. M. Reckendorf and H. Helmut, Chem. Ber., 113, 3089 (1980). The optical rotation and melting point of the compound 5 agree with the reported values.
14. S. Takano, M. Akiyama, S. Sata and K. Ogasawara, Chem. Lett., 1593 (1983).
15. P. Garegg, E. Monica, H. Hans and O. Stefan, J. Carbohydr. Chem., 2, 305 (1983).
16. B. Samuelsson and R. Johansson, J. Chem. Soc., Perkin Trans I, 2371 (1984).
17. D. Seebach and G. Adam, Synthesis, 373(1988).
18. J. B. Etienne, K. C. Duplantier and M. P. DeNinno, Tetrahedron Lett., 36, 669 (1995).
19. G. A. Dilbeck, L. Field, A. A. Gallo, R. Gargiulo, J. Org. Chem., 43, 4593 (1978).
20. M. Fujinaga and Y. Matsushima, Bull. Chem. Soc. Jpn., 37, 185 (1966).
21. M. Fujinaga and Y. Matsushima, Bull. Chem. Soc. Jpn., 37, 468 (1966).
22. D. L. Flynn, R. E. Zelle and P. A. Grieco, J. Org. Chem., 48, 2424 (1983).
23. L. Grehn, K. Gunnarsson and U. Ragnarsson, Acta Chem. Scand., Ser B., 40, 745 (1986).
24. S. Hanessian, Tetrahedron Lett., 16, 1549 (1967).
25. α radiation (λ=0.71069 Å). The structure was solved and refined using the Molecular Structure Corporation teXsan package on a Silicon Graphics R4000 computer.