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Volumn 64, Issue 21, 1999, Pages 7773-7780

First evident generation of purin-2-yllithium: Lithiation of an 8-silyl- protected 6-chloropurine riboside as a key step for the synthesis of 2- carbon-substituted adenosines

Author keywords

[No Author keywords available]

Indexed keywords

2 PURINYLLITHIUM DERIVATIVE; 6 CHLORO 9 (2,3 O ISOPROPYLIDENE 5 O TRITYL BETA DEXTRO RIBOFURANOSYL) 8 (TRIISOPROPYLSILYL)PURINE; ADENOSINE DERIVATIVE; LITHIUM DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0032717557     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9906577     Document Type: Article
Times cited : (22)

References (33)
  • 8
    • 0026337520 scopus 로고
    • The 2-lithio derivative of an 8-azapurine, 3H-1,2,3-triazolo-[4,5-d]pyrimidine, has been generated through a halogen-lithium exchange reaction: Tanji, K.; Kato, H.; Higashino, T. Chem. Pharm. Bull. 1991, 39, 3037-3040.
    • (1991) Chem. Pharm. Bull. , vol.39 , pp. 3037-3040
    • Tanji, K.1    Kato, H.2    Higashino, T.3
  • 11
    • 0000785794 scopus 로고
    • For reports concerning anionic migration of TBDMS and TIPS groups from oxygen to carbon, see: (a) Bures, E. J.; Keay, B. A. Tetrahedron Lett. 1987, 28, 5965-5968.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 5965-5968
    • Bures, E.J.1    Keay, B.A.2
  • 14
    • 0026699017 scopus 로고
    • For a review concerning the Stille reaction, see: Mitchell, T. N. Synthesis 1992, 803-815.
    • (1992) Synthesis , pp. 803-815
    • Mitchell, T.N.1
  • 18
    • 0013814082 scopus 로고
    • This method has been applied to the synthesis of 2-(trifluoro-methyl)adenosine: Gough, G.; Maguire, M. H. J. Med. Chem. 1965, 8, 866-867.
    • (1965) J. Med. Chem. , vol.8 , pp. 866-867
    • Gough, G.1    Maguire, M.H.2
  • 23
    • 33947336041 scopus 로고
    • For the synthesis of 2-carbon-substituted analogues of other purine nucleosides by this method: (a) Yamazaki, A.; Kumashiro, I.; Takenishi, T. J. Org. Chem. 1967, 32, 3258-3260.
    • (1967) J. Org. Chem. , vol.32 , pp. 3258-3260
    • Yamazaki, A.1    Kumashiro, I.2    Takenishi, T.3
  • 33
    • 0011410565 scopus 로고
    • In the lithiation of tert-benzamides, the TMS group has been used to mask the more reactive site ortho to a carboxamide: Mills, R. J.; Snieckus, V. J. Org. Chem. 1983, 48, 1565-1568.
    • (1983) J. Org. Chem. , vol.48 , pp. 1565-1568
    • Mills, R.J.1    Snieckus, V.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.