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Volumn 52, Issue 36, 1996, Pages 11725-11738

Stereocontrolled synthesis of hydroxymethylene phosphonate analogues of phosphorylated tyrosine and their conversion to monofluoromethylene phosphonate analogues

Author keywords

[No Author keywords available]

Indexed keywords

PHENYLALANINE DERIVATIVE; PHOSPHONOAMINO ACID; TYROSINE DERIVATIVE;

EID: 0030565461     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00671-0     Document Type: Article
Times cited : (52)

References (34)
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    • 3. For stereoslective synthesis of L-Pmp derivatives: Cushman, M.; Lee, E.-S. Tetrahedron Lett. 1992, 33, 1193; Dow, R. L.; Bechle, B. M. Synlett 1994, 293; Liu, W.-Q.; Roques, B. P.; Garbay-Jaureguiberry, C. Tetrahedron: Asymmetry 1995, 6, 647.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 1193
    • Cushman, M.1    Lee, E.-S.2
  • 4
    • 36149001822 scopus 로고
    • 3. For stereoslective synthesis of L-Pmp derivatives: Cushman, M.; Lee, E.-S. Tetrahedron Lett. 1992, 33, 1193; Dow, R. L.; Bechle, B. M. Synlett 1994, 293; Liu, W.-Q.; Roques, B. P.; Garbay-Jaureguiberry, C. Tetrahedron: Asymmetry 1995, 6, 647.
    • (1994) Synlett , pp. 293
    • Dow, R.L.1    Bechle, B.M.2
  • 5
    • 0028966998 scopus 로고
    • 3. For stereoslective synthesis of L-Pmp derivatives: Cushman, M.; Lee, E.-S. Tetrahedron Lett. 1992, 33, 1193; Dow, R. L.; Bechle, B. M. Synlett 1994, 293; Liu, W.-Q.; Roques, B. P.; Garbay-Jaureguiberry, C. Tetrahedron: Asymmetry 1995, 6, 647.
    • (1995) Tetrahedron: Asymmetry , vol.6 , pp. 647
    • Liu, W.-Q.1    Roques, B.P.2    Garbay-Jaureguiberry, C.3
  • 8
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    • 5. Waksman, G.; Kominos, D.; Robertson, S. C.; Pant, N.; Baltimore, D.; Birge, R. B.; Cowburn, D.; Hanafusa, H.; Mayer, B. J.; Overduin, M.; Resh, M. D.; Rios, C. B.; Silverman, L.; Kuriyan, J. Nature 1992, 358, 646; Waksman, G.; Shoelson, S. E.; Pant, N.; Cowburn, D., Kuriyan, J. Cell, 1993, 72, 779.
    • (1993) Cell , vol.72 , pp. 779
    • Waksman, G.1    Shoelson, S.E.2    Pant, N.3    Cowburn, D.4    Kuriyan, J.5
  • 10
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    • 2Pmp derivatives: Wrobel, J.; Dietrich, A. Tetrahedron Lett. 1993, 34, 3543; Smyth, M. S.; Burke, T. R., Jr. Tetrahedron Lett. 1994, 35, 551; Solas, D.; Hale, R. L.; Patel, D. V. J. Org. Chem. 1996, 61, 1537 and refernces cited therein.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 3543
    • Wrobel, J.1    Dietrich, A.2
  • 11
    • 0028206694 scopus 로고
    • 2Pmp derivatives: Wrobel, J.; Dietrich, A. Tetrahedron Lett. 1993, 34, 3543; Smyth, M. S.; Burke, T. R., Jr. Tetrahedron Lett. 1994, 35, 551; Solas, D.; Hale, R. L.; Patel, D. V. J. Org. Chem. 1996, 61, 1537 and refernces cited therein.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 551
    • Smyth, M.S.1    Burke T.R., Jr.2
  • 12
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    • and refernces cited therein
    • 2Pmp derivatives: Wrobel, J.; Dietrich, A. Tetrahedron Lett. 1993, 34, 3543; Smyth, M. S.; Burke, T. R., Jr. Tetrahedron Lett. 1994, 35, 551; Solas, D.; Hale, R. L.; Patel, D. V. J. Org. Chem. 1996, 61, 1537 and refernces cited therein.
    • (1996) J. Org. Chem. , vol.61 , pp. 1537
    • Solas, D.1    Hale, R.L.2    Patel, D.V.3
  • 15
    • 0028791169 scopus 로고
    • 10. O-(2-Malonyl)-L-tyrosine derivatives are recently proposed as a hydrolytically stable mimic of pTyr: Ye. B.; Akamatsu, M.; Shoelson, S. E.; Wolf, G.; Giorgetti-Peraldi, S.; Van, X.; Roller, P. P.; Burke, T. R., Jr. J. Med. Chem. 1995, 38, 4270; Burke, T. R., Jr.; Ye, B.; Akamatsu, M.; Ford, H., Jr.; Yan, X.; Kole, H. K.; Wolf, G.; Shoelson, S. E.; Roller, P. P. J. Med. Chem. 1996, 39, 1021.
    • (1995) J. Med. Chem. , vol.38 , pp. 4270
    • Ye, B.1    Akamatsu, M.2    Shoelson, S.E.3    Wolf, G.4    Giorgetti-Peraldi, S.5    Van, X.6    Roller, P.P.7    Burke T.R., Jr.8
  • 16
    • 0029930442 scopus 로고    scopus 로고
    • 10. O-(2-Malonyl)-L-tyrosine derivatives are recently proposed as a hydrolytically stable mimic of pTyr: Ye. B.; Akamatsu, M.; Shoelson, S. E.; Wolf, G.; Giorgetti-Peraldi, S.; Van, X.; Roller, P. P.; Burke, T. R., Jr. J. Med. Chem. 1995, 38, 4270; Burke, T. R., Jr.; Ye, B.; Akamatsu, M.; Ford, H., Jr.; Yan, X.; Kole, H. K.; Wolf, G.; Shoelson, S. E.; Roller, P. P. J. Med. Chem. 1996, 39, 1021.
    • (1996) J. Med. Chem. , vol.39 , pp. 1021
    • Burke T.R., Jr.1    Ye, B.2    Akamatsu, M.3    Ford H., Jr.4    Yan, X.5    Kole, H.K.6    Wolf, G.7    Shoelson, S.E.8    Roller, P.P.9
  • 18
    • 0029655735 scopus 로고    scopus 로고
    • 12. Recently, it is reported that the biological profile of monofluoromethylene phosphonate analogues for sn-glycerol-3-phosphate differs remarkably depending on the configuration of the CHF stereogenic centers: Nieschalk, J.; Batsanov, A. S.; O'Hagan, D.; Howard, J. A. K. Tetrahedron 1996, 52, 165.
    • (1996) Tetrahedron , vol.52 , pp. 165
    • Nieschalk, J.1    Batsanov, A.S.2    O'Hagan, D.3    Howard, J.A.K.4
  • 22
    • 85030278895 scopus 로고    scopus 로고
    • note
    • 3) analysis of the crude reaction mixture.
  • 23
    • 85030269580 scopus 로고    scopus 로고
    • note
    • 17. The methyl ester of 13 and 15 was partially hydrolyzed at the stage of removal of the chiral auxiliary with the acid-treatment. Then, reesterification under the Fisher's conditions was necessary to obtain a good yield of 13 and 15.
  • 28
    • 85030267496 scopus 로고    scopus 로고
    • note
    • 19
  • 29
    • 85030275113 scopus 로고    scopus 로고
    • note
    • Ni pathway could not be excluded since we were unable to accurately determine the stereochemistry of 16, 17 and 20 due to diastereo-or enantiomerically poor state of these phosphonates.
  • 33
    • 85030279516 scopus 로고    scopus 로고
    • note
    • 3) δ 7.38 (2H, d, J=8.2 Hz), 7.16 (2H, d, J=8.2 Hz), 5.80 (1H, s), 4.45 (1H, dq, J-6.7, 6.7 Hz), 4.28-4.12 (1H, m), 2.33 (3H, s), 1.98 (1H, ddd, J=6.2, 12.4, 12.4 Hz), 1.48 (3H, d, J=6.9 Hz), 1.46-1.40 (1H, m), 1.28 (3H, d, J=6.2 Hz).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.