Monomethoxytrityl (MMT) as a versatile amino protecting group for complex prodrugs of anticancer compounds sensitive to strong acids, bases and nucleophiles

Tetrahedron Letters

Volumn 38, Issue 30, 1997, Pages 5257-5260

  Dubowchik, Gene M ^a   Radia, Shilpa ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACID; ANISOLE; ANTINEOPLASTIC AGENT; BASE; CHLOROACETIC ACID; DICHLOROACETIC ACID; DOXORUBICIN; MITOMYCIN C; PACLITAXEL; PRODRUG;

ARTICLE; DRUG SYNTHESIS; TECHNIQUE;

EID: 0030792535     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01158-1     Document Type: Article

References (15)

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2. Dubowchik, G.M.; Firestone, R.A.; Willner, D.; Hofstead, S.J.; Knipe, J.O.; Mosure, K.W.; Lasch, S.J.; and Trail, P.A., manuscript in preparation.
3. Greene, T.W. and Wuts, P.G.M. Protective Groups in Organic Synthesis 2nd Ed. 1991, John Wiley and Sons, New York.
4. Two recent examples of the use of MMT as an amino protecting group: Will, D.W.; Breipohl, G.; Langner, D.; Knolle, J. and Uhlmann, E. Tetrahedron 1995, 51, 12069-12082; Cook, R.M.; Adams, J.H. and Hudson, D. Ttrahedron Letters 1994, 35, 6777-6780.
5. Two recent examples of the use of MMT as an amino protecting group: Will, D.W.; Breipohl, G.; Langner, D.; Knolle, J. and Uhlmann, E. Tetrahedron 1995, 51, 12069-12082; Cook, R.M.; Adams, J.H. and Hudson, D. Ttrahedron Letters 1994, 35, 6777-6780.
6. Barlos, K.; Papaioannou, D. and Theodoropoulos, D. J. Org. Chem. 1982, 47, 1324-1326.
7. All new compounds gave satisfactory NMR, mass spectral, microanalytical and/or HRMS data.
8. Carl, P.L.; Chakravarty, P.K. and Katzenellenbogen, J.A. J. Med. Chem. 1981, 24, 479-480.
9. Dubowchik, G.M. and Firestone, R.A., manuscript in preparation.
10. 18Na: 1183.4488. Found: 1183.4457.
11. A simple tritylamino-Lys version of 10 was prepared and subjected to the same deblocking conditions. After 1h less than 10% of 11 had formed.
12. For synthetic and structural details concerning MMC compounds, see the next communication in this issue.
13. Vyas, D.M. in The Chemistry and Pharmacology of Taxol® and Its Derivatives Farina, V. ed., 1995, Elsevier, Amsterdam, p. 110.
14. Georg, G.I.; Boge, T.C.; Cheruvallath, Z.S.; Clowers, J.S.; Harriman, G.C.B.; Hepperle, M and Park, H. in Taxol®-Science and Applications 1995, CRC Press, Boca Raton, p. 365.
15. 21: 1470.6159. Found: 1470.6135.