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Volumn 48, Issue 48, 2007, Pages 8554-8557

Facile synthesis of 2′-O-cyanoethyluridine by ring-opening reaction of 2,2′-anhydrouridine with cyanoethyl trimethylsilyl ether in the presence of BF3·Et2O

Author keywords

[No Author keywords available]

Indexed keywords

2' O CYANOETHYL 4 N ACETYLCYTIDINE 3' PHOSPHORAMIDITE DERIVATIVE; 2' O CYANOETHYLENEURIDINE 3' PHOSPHORAMIDITE DERIVATIVE; 2' O CYANOETHYLURIDINE; 2,2' ANHYDROURIDINE; 4 (1H 1,2,4 TRIAZOL 1 YL)URIDINE DERIVATIVE; AMMONIA; CYANOETHYL TRIMETHYLSILYL ETHER; OLIGORIBONUCLEOTIDE; PHOSPHORAMIDIC ACID DERIVATIVE; SILANE DERIVATIVE; UNCLASSIFIED DRUG; URIDINE DERIVATIVE;

EID: 35548966577     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.09.105     Document Type: Article
Times cited : (11)

References (30)
  • 16
    • 35548981912 scopus 로고    scopus 로고
    • McGee, D.P.C.; Zhai, Y. Abstracts of American Chemical Society National Meeting, Division of Organic Chemistry, March 1996, paper 253, 1996.
  • 23
    • 35548944177 scopus 로고    scopus 로고
    • note
    • 25 On a large scale (10-20 mmol), however, the yield dropped to 70-80% since this reaction was carried out by a two-phase system where vigorous stirring was essential. On a laboratory scale, it was difficult to stir the two-phase mixture efficiently. Therefore, in the large scale synthesis, the total yield of 2′-O-cyanoethyluridine was ca. 45-50%.
  • 30
    • 35548983214 scopus 로고    scopus 로고
    • note
    • 3-MeOH (98:2, v/v) containing 0.5% triethylamine to give 4-N-acetyl-2′-O-(2-cyanoethyl)-5′-O-(4,4′-dimethoxytrityl)cytidine 3′-(N,N-diisopropyl)phosphoramidite (11) as a white foam (160 mg, 85%).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.