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Synthesis of -amino--keto-esters (-oxodipeptides) |
| XU Yanjie, CHEN Ligong |
| School of Chemical Engineering and Technology, Tianjin University |
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Abstract The synthesis of ?-amino-?-keto-esters (?-oxo dipeptides) was studied. Corresponding ?-amino-?-keto-esters were prepared from BOC-(L)-Valine and BOC-(L)-isoleucine by coupling with (D,L)-threonine hydrochloride and oxidation with Dess-Martin periodinane (DMP) with a total yield of 48% and 38%, respectively.
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Issue Date: 05 December 2008
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| 1 |
Wipf P . Syntheticstudies of biologically active marine cyclopeptides. Chem Rev, 1995, 95(6): 2115-2134.
doi:10.1021/cr00038a013
|
| 2 |
Michael J P, Pattenden G . Marine metabolites and metalion chelation: the facts and the fantasies. Angew Chem Int Ed Engl, 1993, 32: 1-23.
doi:10.1002/anie.199300013
|
| 3 |
Haberhauer G, Rominger F . Syntheses and structuresof imidazole analogues of lissoclinum cyclopeptides. Eur J Org Chem, 2003 : 3209-3218
|
| 4 |
Haberhauer G, Rominger F . Synthesis of a new classof imidazole-based cyclic peptides. TetrahedronLett, 2002, 43: 6335-6338.
doi:10.1016/S0040-4039(02)01365-5
|
| 5 |
Gordon T D, Singh J, Hansen P E, Morgan B A . Syntheticapproaches to the “azole” peptide mimetics. Tetrahedron Lett, 1993, 34: 1901-1904.
doi:10.1016/S0040-4039(00)91958-0
|
| 6 |
Boeckman R K, Shao P C, Mullins J J . The Dess-Martin periodinane: 1,1,1-tri acetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one. Organic Syntheses, 2004, Coll Vol 10: 696; 2000, Vol 77: 141
|
| 7 |
Kigoshi H, Yamada S . Synthesis of dolastatin I,a cytotoxic cyclic hexapeptide from the sea hare dolabella auricularia. Tetrahedron, 1999, 55: 12301-12308.
doi:10.1016/S0040-4020(99)00729-2
|
| 8 |
Singh J, Gordon T D, Earley W G, Morgan B A . An efficientsynthesis and acylation of α-amino-β-keto-esters: Versatileintermediates in the synthesis of peptide mimetics. Tetrahedron Lett, 1993, 34: 211-214.
doi:10.1016/S0040-4039(00)60549-X
|
| 9 |
Suzuki M, Iwasaki T, Miyoshi M, Okumura K, Matsumoto K . Synthesis of amino acidsand related compounds. 6. New convenient synthesis of α-C-acylamino acids and α-amino ketones. J Org Chem, 1973, 38: 3571-3575.
doi:10.1021/jo00960a028
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