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Volumn 47, Issue 52, 2006, Pages 9187-9189

An efficient Mitsunobu coupling to adenine-derived carbocyclic nucleosides

Author keywords

Aristeromycin and neplanocin analogs; Boc protected adenine; Mitsunobu

Indexed keywords

5' HOMOARISTEROMYCIN; ADENINE; ANTIVIRUS AGENT; ARISTEROMYCIN; CARBOCYCLIC NUCLEOSIDE; NEPLANOCIN; UNCLASSIFIED DRUG;

EID: 33751176462     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.10.126     Document Type: Article
Times cited : (46)

References (26)
  • 14
    • 33751164568 scopus 로고    scopus 로고
    • note
    • 8 in dry THF (10 mL) at 0 °C were added dropwise, diisopropyl azodicarboxylate (DIAD) (1.2 mmol). In most cases a pale orange or colorless clear solution was observed immediately following the addition of DIAD. Upon completion of the reaction (by TLC), the mixture was evaporated in vacuo to dryness and the resultant residue purified by flash chromatography. (Chromatography solvents were the mixtures of hexanes and EtOAc.) The reaction conditions and yields are presented in Table 1.
  • 15
    • 33751197640 scopus 로고    scopus 로고
    • 10b produced 3.
  • 16
    • 33751180702 scopus 로고    scopus 로고
    • Deprotection could be accomplished in a good yield by dissolving the requisite precursor in 3 N HCl in MeOH followed by heating at 50 °C overnight. Removal of the solvent was followed by neutralization with IRA-67 resin in MeOH. Evaporation of the reaction mixture yielded a residue that was purified by flash chromatography (EtOAc/MeOH).
  • 17
    • 33751177707 scopus 로고    scopus 로고
    • 10b
  • 21
    • 33751195659 scopus 로고    scopus 로고
    • note
    • Commercially available.
  • 26
    • 33751168641 scopus 로고    scopus 로고
    • note
    • 4Si) 155.4, 152.7, 150.2, 138.7, 120.0, 56.0, 32.8, 23.8.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.