Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(i)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides.
@article{Torne2002PeptidotriazolesOS, title={Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(i)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides.}, author={Christian W. Torn{\o}e and Caspar Elo Christensen and Morten Meldal}, journal={The Journal of organic chemistry}, year={2002}, volume={67 9}, pages={ 3057-64 } }
The cycloaddition of azides to alkynes is one of the most important synthetic routes to 1H-[1,2,3]-triazoles. Here a novel regiospecific copper(I)-catalyzed 1,3-dipolar cycloaddition of terminal alkynes to azides on solid-phase is reported. Primary, secondary, and tertiary alkyl azides, aryl azides, and an azido sugar were used successfully in the copper(I)-catalyzed cycloaddition producing diversely 1,4-substituted [1,2,3]-triazoles in peptide backbones or side chains. The reaction conditions…
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References
SHOWING 1-10 OF 11 REFERENCES
1-Azidoethyl)carbamic Acid 9H-Fluoren-9-ylmethyl Ester, Fmoc-Gly-ψ[CH2N3] (17). Fmoc-Gly-ol (2.02 mmol) afforded 17 (530 mg, 85%) after flash chromatography
- 1-Azidoethyl)carbamic Acid 9H-Fluoren-9-ylmethyl Ester, Fmoc-Gly-ψ[CH2N3] (17). Fmoc-Gly-ol (2.02 mmol) afforded 17 (530 mg, 85%) after flash chromatography
Asp-CO) IR: 1732, 2103 cm -1 . [R] 25 D ) -3° (c ) 1.0, CHCl3)
- Asp-CO) IR: 1732, 2103 cm -1 . [R] 25 D ) -3° (c ) 1.0, CHCl3)
Fmocaromatic protons). 13 C NMR (62.5 MHz, CDCl3): δ ) 13.4, 15.5 and 18.8 (3·Ar-CH3)
- Ar-CH2)
CDCl3): δ ) 1.46 (s, 9H, tert-butyl), 2.53 (d, 2H
- J )
68 mmol) afforded 16 as a syrup (1.11 g, 98%) after flash chromatography (PE/EA 5:1). 1 H NMR
23 (s, 1 H, triazole-H 4 ), 8.31 (m, 1 H, Gly-NH)
Fmoc-CHCH2)
- CDCl3): δ ) 38.5 (Phe-CH2-N3)
N. J. Med. Chem
- N. J. Med. Chem
- 1991
Phe aromatic protons)
3-(9H-fluoren-9-ylmethoxycarbonylamino)- butyric Acid tert-Butyl Ester, Fmoc-Asp(tBu)-ψ[CH2N3] (16). Fmoc-Asp( t Bu)-ol (2.68 mmol) afforded 16 as a syrup (1
- 98%) after flash chromatography (PE/EA 5:1). 1 H NMR