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Volumn 11, Issue 2, 2007, Pages 200-205

Practical synthesis of a heterocyclic immunosuppressive vitamin D analogue

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EID: 34247231581     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op060130d     Document Type: Article
Times cited : (25)

References (21)
  • 12
    • 34247262846 scopus 로고    scopus 로고
    • Chem. Abstr. 1948, 129.
    • Chem. Abstr. 1948, 129.
  • 14
    • 0026509053 scopus 로고    scopus 로고
    • The bromination of 2-hexanone gives besides 1-bromohexan-2-one also the 3-bromoregioisomer: Thomas, A. P.; Allott, C. P.; Gibson, K. H.; Major, J. S.; Masek, B. B.; Oldham, A. A.; Ratcliffe, A. H.; Roberts, D. A.; Russell, S. T.; Thomason, D. A. J. Med. Chem. 1992, 35, 877-885.
    • (a) The bromination of 2-hexanone gives besides 1-bromohexan-2-one also the 3-bromoregioisomer: Thomas, A. P.; Allott, C. P.; Gibson, K. H.; Major, J. S.; Masek, B. B.; Oldham, A. A.; Ratcliffe, A. H.; Roberts, D. A.; Russell, S. T.; Thomason, D. A. J. Med. Chem. 1992, 35, 877-885.
  • 15
    • 0030054110 scopus 로고    scopus 로고
    • For the synthesis of 1-amino-2-hexan-2-one by Gabriel synthesis, see: Brown, P.; Davies, D. T.; O'Hanlon, P. J.; Wilson, J. M. J. Med. Chem. 1996, 39, 446-457.
    • (b) For the synthesis of 1-amino-2-hexan-2-one by Gabriel synthesis, see: Brown, P.; Davies, D. T.; O'Hanlon, P. J.; Wilson, J. M. J. Med. Chem. 1996, 39, 446-457.
  • 16
    • 34247187100 scopus 로고    scopus 로고
    • The reaction of epoxide 19 with ammonia resulted in a mixture of mono-, bis-, and tris(2-hydroxyhex-1-yl)amines; benzylamine and 19 led to a 1:1 mixture of the mono- and bis(2-hydroxyhex-1-yl)benzylamines.
    • The reaction of epoxide 19 with ammonia resulted in a mixture of mono-, bis-, and tris(2-hydroxyhex-1-yl)amines; benzylamine and 19 led to a 1:1 mixture of the mono- and bis(2-hydroxyhex-1-yl)benzylamines.
  • 18
    • 34247249540 scopus 로고    scopus 로고
    • The condensation of 21 and 23 in the presence of diisopropyl carbodimide instead of DCC gave a lower yield of the amide 25.
    • The condensation of 21 and 23 in the presence of diisopropyl carbodimide instead of DCC gave a lower yield of the amide 25.
  • 19
    • 34247262278 scopus 로고    scopus 로고
    • The direct condensation between the ester 22 and alcohol 21 gave a moderate yield (51%) of 25. 2-Hydroxypyridine catalyses this reaction; in a side reaction also 5% of the 1-amino-hex-2-enyl-estar was formed.
    • The direct condensation between the ester 22 and alcohol 21 gave a moderate yield (51%) of 25. 2-Hydroxypyridine catalyses this reaction; in a side reaction also 5% of the 1-amino-hex-2-enyl-estar was formed.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.