A new polymer support silylene linking method for hindered hydroxyl- bearing systems

Journal of Organic Chemistry

Volumn 64, Issue 11, 1999, Pages 4183-4186

  Savin, Kenneth A ^a   Woo, Jonathan C G ^a   Danishefsky, Samuel J ^a,b  

^a MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

^b Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROXYL GROUP; POLYMER; POLYSTYRENE; SILANE DERIVATIVE; SILYLENE; UNCLASSIFIED DRUG;

ARTICLE; CARBOHYDRATE SYNTHESIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; PEPTIDE SYNTHESIS; POLYMERIZATION;

EID: 0033612208     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9820566     Document Type: Article

References (18)

1. (a) Roberge, J. Y.; Beebe, X.; Danishefsky, S. J. Science 1995, 269, 202.
2. (b) Randolph, J. T.; McClure, K. F.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 5712.
3. (c) Danishefsky, S. J.; McClure, K. F.; Randolph, J. T.; Ruggeri, R. B. Science 1993, 260, 1307.
4. Behar, V.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1468.
5. Randolph, J. T.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1470.
6. Zheng, C.; Seeberger, P. H.; Danishefsky, S. J. J. Org. Chem. 1998, 63, 1126.
7. (a) Huang, W.-Q. J. Chem. Soc., Chem. Commun. 1985, 909.
8. (b) Rootledge, A.; Wallis, M. P.; Ross, K. C.; Fraser, W. An Efficient Deprotection Strategy for Automated Oligonucleotide Synthesis Using A Novel Silyl Linked Solid Support. Solid-Phase Synthesis and Combinatorial Libraries; Mayflower Scientific Limited: Birmingham, U.K., 1996; pp 147.
9. The hydroxy-modified Merrifield and Wang resins (hydroxymethyl resin) were purchased from Bachem Bioscience Inc. and used without further manipulation.
10. Arkles, B. In Silanes, Kirk-Othmer Encyclopedia of Chemical Technology, 4th ed.; John Wiley & Sons: New York, 1997; Vol. 22, pp 38.
11. Gallant, M.; Link, J. T.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 343.
12. (b) Hadfield, A. F.; Sartorelli, A. C. Carbohydr. Res. 1982, 101, 197.
13. (c) Horton, D.; Weckerle, W. Carbohdyr. Res. 1988, 174, 305.
14. (d) Park, T. K.; Kim, I. J.; Hu, S.; Bilodoeau, M.; Randolph, J. T.; Kwon, O.; Danishefsky, S. J. J. Am. Chem. Soc. 1996, 116, 11488.
15. Roberge, J. T.; Beebe, X.; Danishefsky, S. J. J. Am. Chem. Soc. 1998, 120, 3915
16. (a) Kiso, Y.; Yajima, H. J. Chem. Soc., Chem. Commun. 1972, 942.
17. (b) Anisfeld, S. T.; Lansbury, P. T., Jr. J. Org. Chem. 1990, 55, 5560.
18. Matsuura, S.; Niu, C.-H.; Cohen, J. N. J. Chem. Soc., Chem. Commun. 1976, 451.