Orthogonally protected dialkynes

Tetrahedron Letters

Volumn 37, Issue 44, 1996, Pages 7959-7962

  Ernst, Alexander ^a   Gobbi, Luca ^a   Vasella, Andrea ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030605109     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01838-2     Document Type: Article

References (34)

1. 1. Oligosaccharide Analogues of Polysaccharides: Part 10. Xu, J.; Egger, A.; Bernet, B.; Vasella A. Helv. Chim. Acta 1996 submitted.
2. 1. Oligosaccharide Analogues of Polysaccharides: Part 10. Xu, J.; Egger, A.; Bernet, B.; Vasella A. Helv. Chim. Acta 1996 submitted.
3. 2. Alzeer, J; Cai, C.; Vasella, A. Helv. Chim. Acta 1995, 78, 242-264.
4. 3. see also: a) Igner E.; Paynter, O. I.; Simmonds, D. J.; Whiting, M. C. J. Chem. Soc., Perkin Trans. 1 1987, 2447-2454.
5. b) Young, J. K.; Moore, J. S. "Acetylenes in Nanostructures". In Modern Acetylene Chemistry ; Stang, P.J.; Diederich, F. Eds.; VCH, Weinheim, 1995; pp. 415-442 and references quoted there.
6. c) Tour, J. M. Chem. Rev. 1996, 96, 537-553 and references quoted there.
7. d) Liess, P.; Hensel, V.; Schlütter, A.-D.; Liebigs Ann. 1996, 1037-1040.
8. e) Langweiler, U. D.; Fritz, M. G.; Seebach, D. Helv. Chim. Acta 1996, 79, 670-701.
9. f) Z. Huang, Diss. ETH No. 10429, Eidgenössische Technische Hochschule Zürich 1993.
10. g) Koto, S.; Uchida, T.; Zen, S. Bull. Chem. Soc. Jpn. 1973, 46, 2520.
11. 4. Barany, G.; Merrifield, R.B. J. Am. Chem. Soc. 1977, 99, 7363-7365.
12. 5. a) Haseltine, J. N.; Cabal, M. P.; Mantlo, N. B.; Iwasawa, N.; Yamashita, D. S.; Coleman, R. S.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1991, 113, 3850-3866. Myers, A. G.; Harrington, P. M.; Kuo, E. Y. J. Am. Chem. Soc. 1991, 113, 694-695.
13. 5. a) Haseltine, J. N.; Cabal, M. P.; Mantlo, N. B.; Iwasawa, N.; Yamashita, D. S.; Coleman, R. S.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1991, 113, 3850-3866. Myers, A. G.; Harrington, P. M.; Kuo, E. Y. J. Am. Chem. Soc. 1991, 113, 694-695.
14. b) Anderson, H. L.; Sanders, J. K. M. J. Chem. Soc., Perkin Trans. 1 1995, 2223-2229. Arnold, D. P.; Nitschinsk, L. J. Tetrahedron Lett. 1992, 48, 8781-8782.
15. b) Anderson, H. L.; Sanders, J. K. M. J. Chem. Soc., Perkin Trans. 1 1995, 2223-2229. Arnold, D. P.; Nitschinsk, L. J. Tetrahedron Lett. 1992, 48, 8781-8782.
16. c) Diederich, F. "Oligoacetylenes". In Modern Acetylene Chemistry ; Stang, P.J.; Diederich, F. Eds.; VCH, Weinheim, 1995; pp. 443-471 and references quoted there. Grubbs, R.; Kratz, D. Chem. Ber. 1993, 126, 149-157.
17. c) Diederich, F. "Oligoacetylenes". In Modern Acetylene Chemistry ; Stang, P.J.; Diederich, F. Eds.; VCH, Weinheim, 1995; pp. 443-471 and references quoted there. Grubbs, R.; Kratz, D. Chem. Ber. 1993, 126, 149-157.
18. 6. Ernst, A.; Vasella, A. Helv. Chim. Acta 1996, 79, 1279-1294 and earlier papers in this series.
19. 7. Cai, C.; Vasella, A. Helv. Chim. Acta 1995, 78, 732-756. The authors suggested the acronym DOPS-alkynes = {[dimethyl(oxy)propyl]dimethylsilyl}-alkyne for a series of dimethyl-[1,1-dimethyl-3-(tetrahydro-2H-pyran-2-yloxy)propyl]silyl-protected alkyne building blocks.
20. 8. Cai, C.; Vasella, A. Helv. Chim. Acta 1996, 79, 255-268. Ernst, A.; Bürli, R., Vasella A. unpublished results.
21. 8. Cai, C.; Vasella, A. Helv. Chim. Acta 1996, 79, 255-268. Ernst, A.; Bürli, R., Vasella A. unpublished results.
22. 3).
23. 10. a) Mironov, V.F.; Kravchenko, A.L. Bull. Acad. Sci. USSR, Chem. Sci. (Engl. Transl.) 1965, 988-995.
24. b) purchased from Fluka or prepared according to Brandsma, L. Preparative Acetylenic Chemistry (second Edition); Elsevier, Amsterdam, 1988; pp. 114-117.
25. 11. Huynh, C.; Linstrumelle, G. Tetrahedron 1988, 44, 6337-6344.
26. 12. Chemin, D.; Linstrumelle, G. Tetrahedron 1994, 50, 5335-5344.
27. 13. Tilley, J. W.; Zawoisky, S. J. Org. Chem. 1988, 53, 386-390.
28. 12NBrGe (298.73): C 40.21, H 4.05; found C 40.06, H 4.09.
29. 15. Purchased from Aldrich and used without further purification.
30. 19.
31. 17. The reaction should be monitored carefully by tlc and worked up as soon as the starting material has been consumed.
32. 3).
33. 3).
34. 20. McQuilkin, R. M.; Garratt, P. J.; Sondheimer, F. J. Am. Chem. Soc. 1970, 92, 6682-6683.