An improved synthesis and selective coupling of a hydroxy based photolabile linker for solid phase organic synthesis

Tetrahedron Letters

Volumn 38, Issue 45, 1997, Pages 7851-7852

  Whitehouse, Darren L ^a   Savinov, Sergey N ^a   Austin, David J ^a  

^a YALE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANIC COMPOUND; REAGENT; RESIN;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ESTERIFICATION; ORGANIC CHEMISTRY; PHOTOLYSIS; REACTION ANALYSIS; SYNTHESIS;

EID: 0030730054     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10133-2     Document Type: Article

References (10)

1. Rich, D. H.; Gurwara, S. K. J. Chem. Soc., Chem. Commun. 1973, 610-611.
2. Lloyd-Williams, P.; Albericio, F.; Giralt, E. Tetrahedron 1993, 49, 11065-11133.
3. Holmes, C. P.; Jones, D. G. J. Org. Chem. 1995, 60, 2318-2319.
4. Yoo, D. J.; Greenberg, M. M. J. Org. Chem. 1995, 60, 3358-3364.
5. Novabiochem Corp., under an exclusive license from Affymax Research Institute.
6. Holmes, C. P. J. Org. Chem. 1997, 62, 2370-2380.
7. Wang, S. W. J. Org. Chem. 1976, 41, 3258-3261.
8. Bodanszky, M.; Bodanszky, A. The Practice of Peptide Synthesis; 2nd Ed.; Springer-Verlag: N Y, 1994.
9. Le Nguyen, D.; Seyer, R.; Heitz, A.; Castro, B. J. Chem. Soc., Perkin Trans 1 1985, 1025-1031.
10. Photolinker 1 (2.0 eq.), BOP (2.0 eq.), HOBt (2.0 eq.), DIPEA (3.0 eq.) were added consecutively to a suspension of Wang resin (1.0 eq.) in methylene chloride (10 mL per gram resin). The resultant mixture was rotated at room temperature for 24 hours, filtered, and washed to yield the photolinker resin 2.