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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.
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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.
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28
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0029012602
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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.
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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.
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31
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0028240870
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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.
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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.
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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.
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