Non-acidic cleavage of wang-derived ethers from solid support: Utilization of a mixed-bed scavenger for DDQ

Tetrahedron Letters

Volumn 38, Issue 28, 1997, Pages 4973-4976

  Deegan, Tracy L ^a   Gooding, Owen W ^a   Baudart, Sylvie ^a   Porco Jr , John A ^a  

^a Argonaut Technologies   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ETHER DERIVATIVE; RESIN;

ACETYLATION; ARTICLE; NUCLEAR MAGNETIC RESONANCE; OXIDATION; STOICHIOMETRY; SYNTHESIS;

EID: 0030873736     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01078-2     Document Type: Article

References (21)

1. For recent reviews on solid-phase organic synthesis, see: (a) Balkenhohl, F.; von dem Bussche-Hunnefeld, Lansky, A.; Zechel, C. Angew. Chem. Int. Ed. Engl. 1996, 35, 2288.
2. (b) Thompson, L.A.; Ellman, J.A. Chem Rev. 1996, 96, 555.
3. (c) Fruchtel, J.S.; Jung, G. Angew, Chem. Int. Ed. Engl. 1996, 35, 17.
4. (d) Hermkens, P.H.H.; Ottenheijm, H.C.J.; Rees, D. Tetrahedron 1996, 52, 4527.
5. (a) Frechet, J.M.J.; Nuyens, L.J. Can. J. Chem. 1976, 54, 926.
6. (b) Fyles, T.M.; Leznoff, C.C. Can. J. Chem. 1976, 54, 935.
7. Alsina, J.; Chiva, C.; Ortiz, M.; Rabanal, F.; Giralt, E.; Albericio, F. Tetrahedron Lett. 1997, 38, 883.
8. Thompson, L.A.; Ellman, J.A. Tetrahedron Lett. 1994, 35, 9333.
9. Farrall, M.J.; Frechet, J.M.J. J. Org. Chem. 1976, 24, 3877.
10. Horita, K.; Yoshioka, T.; Tanaka, T.; Oikawa, Y.; Yonemitsu, O. Tetrahedron 1986, 42, 3021 and references cited therein.
11. ArgoGel-Wang-Cl resin is commercially available from Argonaut Technologies, San Carlos, CA.
12. For a recent paper on the preparation of Wang halide linkers for sulfonamide formation/cleavage see: Ngu, K.; Patel, D.V. Tetrahedron Lett. 1997, 38, 973.
13. 2O, and 5 × THF (10 minute agitations). The resin was washed further with 4 × DCM, 4 × MeOH, and dried in a high-vacuum desiccator overnight.
14. For the use of resins as scavengers, see: (a) Gayo, L.M.; Suto, M.J. Tetrahedron Lett. 1997, 38, 513.
15. (b) Kaldor, S.W.; Siegel, M.G.; Fritz, J.E.; Dressman, B.A.; Hahn, P.J. Tetrahedron Lett. 1996, 37, 7193.
16. Amberlyst® A-26 is a registered trademark of the Rohm and Haas Company.
17. For the reduction of excess DDQ with ascorbic acid, see: Fukase, K.; Yoshimura, T.; Kotani, S.; Kusumoto, S. Bull. Chem. Soc. Jpn., 1994, 67, 473-482
18. - form, Aldrich) was washed with 15 × 1 L water, 6 × 1 L methanol, and 6 × 1 L acetone, and dried under vacuum (60 °C, 12 h). The beads were subsequently transferred to a glass column, flushed with nitrogen, and washed with 3 × 1 L 1.0 N NaOH for 1 h. The resin was washed with water until a neutral pH was obtained (4 × 1 L). 0.4 N Ascorbic Acid was passed through the column for 2 h (3 × 1 L), and the beads finally washed with 4 × 1 L water, 4 × 1 L MeOH, and 4 × 1 L acetone. The ascorbate beads were dried in a high vacuum desiccator for 72 h and stored under nitrogen.
19. Hodge, P.; Ji-Long, J.; Owen, G.J.; Houghton, M.P. Polymer, 1996, 37, 5059.
20. - resin (400 mg, -3.8 mmol/g, 1.40 mmol, 10 equiv. relative to DDQ)) was weighed into a 12 mL polypropylene cartridge. The cleavage solution and 3 × 2 mL DCM washes were then filtered onto the mixed-bed resin. The filtrate was agitated with the mixed-bed resin for 1 hour at 25 °C. The solution and 3 × 2 mL DCM resin washes were collected by filtration and concentrated.
21. For a discussion of linkers that utilize staged-release, see Ref 1 (a) and refs. cited therein.