Combinatorial method for the synthesis of α-hydroxy phosphonates on Wang resin

Tetrahedron Letters

Volumn 37, Issue 34, 1996, Pages 6073-6076

  Cao, Xiaodong ^a   Mjalli, Adnan M M ^a  

^a Ontogen Corporation   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; POLYMER; RESIN;

ARTICLE; REACTION ANALYSIS; SOLID; SYNTHESIS;

EID: 0030593622     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01294-4     Document Type: Article

References (14)

1. 1. Sikorski, J. A.; Miller, M. J.; Braccolino, D. S.; Cleary, D. G.; Corey, S. D.; Font, J. L.; Gruys, K. J.; Han, C. Y.; Lin, K. C.; Pansegrau, P. D.; Ream, J. E.; Schnur, D.; Shah, A.; Walker, M. C. Phosphorus, Sulfur and Silicon 1993, 76, 115.
2. 2. Stowasser, B.; Budt, K-H.; Jian-Qi, L.; Peyman, A.; Ruppert, D. Tetrahedron Lett. 1989, 33, 6625.
3. 3. (a) Patel, D. V.; Rielly-Gauvin, K.; Ryono, D. E. Tetrahedron Lett. 1990, 31, 5587;
4. (b) Patel, D. V.; Rielly-Gauvin, K.; Ryono, D. E. Tetrahedron Lett. 1990, 31, 5591.
5. 4. (a) Burke, T. R., Jr.; Barchi, J. J., Jr.; George, C.; Wolf, G.; Shoelson, S. E.; Van, X. J. Med. Chem. 1995, 38, 1386;
6. (b) Burke, T. R., Jr.; Kole, H. K.; Roller, P. P. Biochem. Biophys. Res. Commun. 1994, 204, 129.
7. 5. Evans, D. A.; Hurst, K. M.; Takacs, J. M. J. Am. Chem. Soc. 1978, 100, 3467.
8. 6. Hammerschmidt, F. Liebigs Ann. Chem. 1988, 955.
9. 7. Marugg, J. E.; Tromp, M.; Kuyl-Yeheskiely, E.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 1986, 27, 2661.
10. 2O. During addition to the resin, the pH of the mixture was kept below 8.5.
11. 9. Froehler, B. C.; Matteucci, M. D. Tetrahedron Lett. 1986, 27, 469.
12. 10. Acid labile alcohols such as t -butyl and electron rich benzyls such as 2,4-dimethoxy benzyl are cleaved during TFA treatment to provide the corresponding phosphate derivatives.
13. 11. A wide range of aldehydes such as straight/branched aliphatics and electron rich/poor aromatics can be used in this reaction.
14. 1H-NMR (400 MHz, d-acetone/10% d-methanol) δ 4.62 (s, 2H); 5.13 (d, 1H, J = 13.2 Hz); 6.64-7.38 (m, 9H). required 295.9, found 294.7.