Phenyl-EDOTn derivatives as super acid labile carboxylic acid protecting groups for peptide synthesis

Tetrahedron Letters

Volumn 49, Issue 20, 2008, Pages 3304-3307

  Isidro Llobet, Albert ^a   Álvarez, Mercedes ^a   Albericio, Fernando ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

Acid labile protecting groups; Carboxylic acid protection; EDOT; EDOTn; Peptide synthesis

Indexed keywords

3,4 ETHYLENEDIOXYTHENYL ALCOHOL; 3,4 ETHYLENEDIOXYTHIOPHENE; 5 (3,4 DIMETHOXYPHENYL) 3,4 ETHYLENEDIOXYTHENYL ALCOHOL; 5 (3,4,5 TRIMETHOXYPHENYL) 3,4 ETHYLENEDIOXYTHENYL ALCOHOL; 5 (4 METHOXYPHENYL) 3,4 ETHYLENEDIOXYTHENYL ALCOHOL; 5 PHENYL 3,4 ETHYLENEDIOXYTHENYL ALCOHOL; ALCOHOL; CARBOXYLIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; PEPTIDE SYNTHESIS;

EID: 42049123240     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.03.074     Document Type: Article

References (11)

1. Tulla-Puche J., Bayó-Puxan N., Moreno J.A., Francesch A.M., Cuevas C., Álvarez M., and Albericio F. J. Am. Chem. Soc. 129 (2007) 5322-5323
2. Kates S.A., Solé N.A., Johnson C.R., Hudson D., Barany G., and Albericio F. Tetrahedron Lett. 34 (1993) 1549-1552
3. Jensen K.J., Alsina J., Songster M.F., Vagner J., Albericio F., and Barany G. J. Am. Chem. Soc. 120 (1998) 5441-5452
4. Jou G., González I., Albericio F., Lloyd-Williams P., and Giralt E. J. Org. Chem. 62 (1997) 354-366
5. Jessing M., Brandt M., Jensen K.J., Cristensen J.B., and Boas U. J. Org. Chem. 71 (2006) 6734-6741
6. Isidro-Llobet, A.; Just-Baringo, X.; Álvarez, M.; Albericio, F. Biopolymers. 2008, doi:10.1002/bip.20823.
7. In: Miyaura N. (Ed). Topics in Current Chemistry (2002), Springer Verlag, Berlin Heidelbert
8. 3): δ = 6.35 (s, 1H), 5.11 (s, 2H), 4.22 (m, 4H), 2.08 (s, 3H). 5-Iodo-3,4-ethylenedioxythenyl acetate (6)3,4-Ethylenedioxythenyl acetate (760 mg, 3.56 mmol) was dissolved in dry DMF (5.5 mL), and NIS (958 mg, 4.27 mmol) was added.
9. 3): δ = 7.62 (d, 2H, J = 8.9 Hz), 7.33 (m, 6H), 7.19 (m, 3H), 7.05 (m, 2H), 6.91 (d, 2H, J = 8.9 Hz), 5.25-5.06 (m, 5H), 4.70 (m, 1H), 4.28 (m, 4H), 3.83 (s, 3H), 3.12 (m, 2H).
10. 2O-AcCN, and analyzed by HPLC. The removal percentage was calculated by comparing the areas at λ = 220 nm of the peaks corresponding to the free and protected amino acid.
11. Fujino M., Wakimasu M., and Kitada C. Chem. Pharmacol. Bull. 29 (1981) 2825-2831