The use of tin(IV) chloride for mild and selective boc deprotection on TFA cleavable Rink-amide MBHA resin

Synlett

Volumn , Issue 13, 2009, Pages 2097-2100

  Freeman, Noam S ^a   Gilon, Chaim ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

Boc; Deprotection; Orthogonal protecting groups; Rink amide MBHA resin; SPOS; SPPS

Indexed keywords

AMIDE; CHLORIDE; CYCLOPEPTIDE; DICHLOROMETHANE; RESIN; TIN CHLORIDE;

ARTICLE; CHEMICAL BOND; DEPROTECTION REACTION; SOLID PHASE SYNTHESIS;

EID: 68949097675     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1217547     Document Type: Article

References (13)

1. Zhang, A. J.; Russell, D. H.; Zhu, J. P.; Burgess, K. Tetrahedron Lett. 1998, 39, 7439.
2. Trivedi, H. S.; Anson, M.; Steel, P. G.; Worley, J. Synlett 2001, 1932.
3. Lejeune, V.; Martinez, J.; Cavelier, F. Tetrahedron Lett. 2003, 44, 4757.
4. Boeglin, D.; Bonnet, D.; Hibert, M. J. Comb. Chem. 2007, 9, 487.
5. Frank, R.; Schutkowski, M. Chem. Commun. 1996, 2509.
6. Miel, H.; Rault, S. Tetrahedron Lett. 1997, 38, 7865.
7. 4. All other experiments were conducted without prior purification of the reagent.
8. Novabiochem® : Novabiochem Catalog 2006/2007, 3.4.
9. Gude, M.; Ryf, J.; White, P. D. Lett. Pept. Sci. 2002, 9, 203.
10. 4 reacting with the peptideresin amide bond is considerably higher and we would expect a greater loss of substrate through cleavage.
11. Kaiser, E.; Colescott, R. L.; Bossinger, C. D.; Cook, P. I. Anal. Biochem. 1970, 34, 595.
12. Christensen, T. Acta Chem. Scand., Ser. B 1979, 33, 763.
13. 2 release and the resin became a bright red color. The resin was then washed with DMF (1 x 3 min), 20% MeOH in DMF (1 x 3 min), 10% DIEA in DMF (1 x 3 min) and DMF (2 x 2 min). The initial wash with DMF instantly restored the resin to its original color.