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Volumn 62, Issue 11, 1997, Pages 3440-3448

Practical, stereoselective synthesis of palinavir, a potent HIV protease inhibitor

Author keywords

[No Author keywords available]

Indexed keywords

ANTIVIRUS AGENT; PALINAVIR; PROTEINASE INHIBITOR;

EID: 8544222655     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9702655     Document Type: Article
Times cited : (79)

References (60)
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    • Unpublished results
    • Unpublished results.
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    • N,N-Dibenzyl-L-phenylalaninol (11) is commercially available from the Nutrasweet Company
    • N,N-Dibenzyl-L-phenylalaninol (11) is commercially available from the Nutrasweet Company.
  • 45
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    • See references cited in: (a) Gillard, J.; Abraham, A.; Anderson, P. C.; Beaulieu, P. L.; Bogri, T.; Bousquet, Y.; Grenier, L.; Guse, I.; Lavallée, P. J. Org. Chem. 1996, 61, 2226-2231. (b) Skiles, J. W.; Giannousis, P. P.; Fales, K. R. Bioorg. Med. Chem. Lett. 1996, 6, 963-966.
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    • This is not a true resolution process per se, since hydroxy amides 18a,b are diastereomeric in nature
    • This is not a true resolution process per se, since hydroxy amides 18a,b are diastereomeric in nature.
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    • Davis, J. W., Jr. J. Org. Chem. 1959, 24, 1691-1694. The acid chloride crystallized as pale yellow needles in 82% yield: mp 94-96 °C dec [lit. mp 96-97 °C].
    • (1959) J. Org. Chem. , vol.24 , pp. 1691-1694
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    • Gross, E.; Meienhofer, J., Eds.; Academic Press Inc.: New York
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    • (1979) The Peptides , vol.1 , pp. 315
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    • note
    • The authors have deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Center. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Center, 12 Union Road, Cambridge CB2 1EZ, U.K.
  • 59
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    • The order and rate of addition, the use of dilute solutions, and efficient stirring are important, to avoid precipitation of the monohy- drochloride salt of 1
    • The order and rate of addition, the use of dilute solutions, and efficient stirring are important, to avoid precipitation of the monohy- drochloride salt of 1.
  • 60
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    • note
    • The free base of 4-picoylyl chloride is unstable and polymerizes if the etheral solution is concentrated to dryness. Addition of DMF before removal of ether ensures the free base remains as a dilute solution, thus reducing the extent of self-condensation. The polymerization process is also minimized if the solutions are kept cold.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.