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Volumn 61, Issue 14, 1996, Pages 4666-4675

Ready access to fluorinated phosphonate mimics of secondary phosphates. Synthesis of the (α,α-Difluoroalkyl)phosphonate analogues of L-Phosphoserine, L-Phosphoallothreonine, and L-Phosphothreonine

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOFLUORINE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE;

EID: 0029885050     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9604752     Document Type: Article
Times cited : (128)

References (58)
  • 13
    • 0029924009 scopus 로고    scopus 로고
    • For syntheses of 4b, see: (a) Solas, D.; Hale, R. L.; Patel, D. V. J. Org. Chem. 1996, 61, 1537-1539. (b) Smyth, M. S.; Burke, T. R., Jr. Tetrahedron Lett. 1994, 35, 551-554. (c) Burke, T. R., Jr.; Smyth, M. S.; Otaka, A.; Roller, P. P. Tetrahedron Lett. 1993, 34, 4125-4128. (d) Wrobel, J.; Dietrich, A. Tetrahedron. Lett. 1993, 34, 3543-3546.
    • (1996) J. Org. Chem. , vol.61 , pp. 1537-1539
    • Solas, D.1    Hale, R.L.2    Patel, D.V.3
  • 14
    • 0028206694 scopus 로고
    • For syntheses of 4b, see: (a) Solas, D.; Hale, R. L.; Patel, D. V. J. Org. Chem. 1996, 61, 1537-1539. (b) Smyth, M. S.; Burke, T. R., Jr. Tetrahedron Lett. 1994, 35, 551-554. (c) Burke, T. R., Jr.; Smyth, M. S.; Otaka, A.; Roller, P. P. Tetrahedron Lett. 1993, 34, 4125-4128. (d) Wrobel, J.; Dietrich, A. Tetrahedron. Lett. 1993, 34, 3543-3546.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 551-554
    • Smyth, M.S.1    Burke Jr., T.R.2
  • 15
    • 0027316389 scopus 로고
    • For syntheses of 4b, see: (a) Solas, D.; Hale, R. L.; Patel, D. V. J. Org. Chem. 1996, 61, 1537-1539. (b) Smyth, M. S.; Burke, T. R., Jr. Tetrahedron Lett. 1994, 35, 551-554. (c) Burke, T. R., Jr.; Smyth, M. S.; Otaka, A.; Roller, P. P. Tetrahedron Lett. 1993, 34, 4125-4128. (d) Wrobel, J.; Dietrich, A. Tetrahedron. Lett. 1993, 34, 3543-3546.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 4125-4128
    • Burke Jr., T.R.1    Smyth, M.S.2    Otaka, A.3    Roller, P.P.4
  • 16
    • 0027318389 scopus 로고
    • For syntheses of 4b, see: (a) Solas, D.; Hale, R. L.; Patel, D. V. J. Org. Chem. 1996, 61, 1537-1539. (b) Smyth, M. S.; Burke, T. R., Jr. Tetrahedron Lett. 1994, 35, 551-554. (c) Burke, T. R., Jr.; Smyth, M. S.; Otaka, A.; Roller, P. P. Tetrahedron Lett. 1993, 34, 4125-4128. (d) Wrobel, J.; Dietrich, A. Tetrahedron. Lett. 1993, 34, 3543-3546.
    • (1993) Tetrahedron. Lett. , vol.34 , pp. 3543-3546
    • Wrobel, J.1    Dietrich, A.2
  • 18
    • 0028838971 scopus 로고
    • (a) Hunter, T. Cell 1995, 80, 225-236.
    • (1995) Cell , vol.80 , pp. 225-236
    • Hunter, T.1
  • 19
    • 0028484480 scopus 로고
    • (b) Cohen, P. BioEssays 1994, 16 (8), 583-588.
    • (1994) BioEssays , vol.16 , Issue.8 , pp. 583-588
    • Cohen, P.1
  • 22
    • 0026661583 scopus 로고
    • (e) Cohen, P. TIBS 1992, 17, 408-413.
    • (1992) TIBS , vol.17 , pp. 408-413
    • Cohen, P.1
  • 28
    • 0029012602 scopus 로고
    • To our knowledge, no data are available on the effectiveness of L-phosphoallothreonine-containing peptides as substrates. However, the technology now appears to be in place to probe this question more readily: Fischer, P. M.; Sandosham, J. Tetrahedron Lett. 1995, 36, 5409-5412.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 5409-5412
    • Fischer, P.M.1    Sandosham, J.2
  • 29
    • 0027984005 scopus 로고
    • For previously reported syntheses of 5, see: (a) Berkowitz, D. B.; Shen, Q.; Maeng, J.-H. Tetrahedron Lett. 1994, 35, 6445-6448. (b) Otaka, A.; Miyoshi K.; Burke, T. R., Jr.; Roller, P. P.; Kubota, H.; Tamamura, H.; Fujii, N. Tetrahedron Lett. 1995, 36, 927-930.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 6445-6448
    • Berkowitz, D.B.1    Shen, Q.2    Maeng, J.-H.3
  • 31
    • 0028240870 scopus 로고
    • For syntheses of the nonhalogenated phosphonate analogues of L-phosphothreonine and L-phosphoallothreonine, see: (a) Ojea, V.; Ruiz, M.; Shapiro, G.; Pombo-Villar, E. Tetrahedron Lett. 1994, 35, 3273-3276. (b) Ruiz, M.; Ojea, V.; Shapiro, G.; Weber, H.-P.; Pombo-Villar, E. Tetrahedron Lett. 1994, 35, 4551-4554.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 3273-3276
    • Ojea, V.1    Ruiz, M.2    Shapiro, G.3    Pombo-Villar, E.4
  • 32
    • 0028303642 scopus 로고
    • For syntheses of the nonhalogenated phosphonate analogues of L-phosphothreonine and L-phosphoallothreonine, see: (a) Ojea, V.; Ruiz, M.; Shapiro, G.; Pombo-Villar, E. Tetrahedron Lett. 1994, 35, 3273-3276. (b) Ruiz, M.; Ojea, V.; Shapiro, G.; Weber, H.-P.; Pombo-Villar, E. Tetrahedron Lett. 1994, 35, 4551-4554.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 4551-4554
    • Ruiz, M.1    Ojea, V.2    Shapiro, G.3    Weber, H.-P.4    Pombo-Villar, E.5
  • 36
    • 0026759367 scopus 로고
    • Yang, Z.-Y.; Burton, D. J. J. Org. Chem. 1992, 57, 4676-4683. These workers do report one example of an analogue of a secondary phosphate derived from the addition of diethyl iodo(difluoromethyl)-phosphonate to cyclohexene (69%).
    • (1992) J. Org. Chem. , vol.57 , pp. 4676-4683
    • Yang, Z.-Y.1    Burton, D.J.2
  • 42
    • 33845183494 scopus 로고
    • and references therein
    • Burton, D. J.; Sprague, J. Org. Chem. 1989, 54, 613-617 and references therein.
    • (1989) J. Org. Chem. , vol.54 , pp. 613-617
    • Burton, D.J.1    Sprague2
  • 49
    • 3343010491 scopus 로고    scopus 로고
    • note
    • The threo THP-ethers apparently decompose to, as yet unidentified, polar byproducts. That only the allothreo alcohol 28 was obtained could be confirmed by reprotection of this alcohol (DHP, PPTS, see Experimental Section) to give only two (27a and 27d) of the original four THP ethers.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.