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Volumn 65, Issue 6, 2000, Pages 1623-1628

(1S)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-hydroxyethylammonium benzoate, a versatile building block for chiral 2-aminoalkanols: Concise synthesis and application to nelfinavir, a potent HIV-protease inhibitor

Author keywords

[No Author keywords available]

Indexed keywords

1 (2,2 DIMETHYL 1,3 DIOXOLAN 4 YL) 2 HYDROXYETHYLAMMONIUM BENZOATE; NELFINAVIR; PROTEINASE INHIBITOR; UNCLASSIFIED DRUG;

EID: 0034708584     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991793e     Document Type: Article
Times cited : (56)

References (38)
  • 28
    • 4243753456 scopus 로고
    • (b) Dressman, B. A.; Fritz, J. E.; Hammond, M.; Hornback, W. J.; Kaldor, S. W.; Kalish, V. J.; Munroe, J. E.; Reich, S. H.; Tatlock, J. H.; Shepherd, T. A.; Rodriguez, M. J. U. S. Patent 5,484,926, 1994 (Agouron Pharmaceuticals, Inc.); Chem. Abstr. 1995, 123, 256539v.
    • (1995) Chem. Abstr. , vol.123
  • 31
    • 0342577670 scopus 로고    scopus 로고
    • note
    • The isomerization was carried out in the presence of 2,2-dimethoxypropane (10 mol %) preventing hydrolysis of acetonide, see Experimental Section.
  • 32
    • 0343011970 scopus 로고    scopus 로고
    • note
    • R = 5.6 min (8, 6.6%), 6.8 min (12, 91.4%), 7.5 min (unidentifiable isomer, 2.0%).
  • 33
    • 0017302164 scopus 로고
    • See Supporting Information in ref 13, also
    • Elliott, W. J.; Fried, J. J. Org. Chem. 1976, 41, 2469. See Supporting Information in ref 13, also.
    • (1976) J. Org. Chem. , vol.41 , pp. 2469
    • Elliott, W.J.1    Fried, J.2
  • 37
    • 0343011969 scopus 로고    scopus 로고
    • note
    • See Supporting Information. The atomic coordinates have been deposited with Cambridge Crystallographic Data Center, 12 Union Road, Cambridge, CB2 1EZ, UK.
  • 38
    • 0343883413 scopus 로고    scopus 로고
    • note
    • The enantiomer of 18 and that of 22 were obtained from 1b by the identical methods to those used in the preparation of 18 and 22 from 1a, respectively.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.