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Volumn 49, Issue 41, 2008, Pages 5890-5893

Efficient loading of primary alcohols onto a solid phase using a trityl bromide linker

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; AZIRIDINE; POLYSTYRENE DERIVATIVE; REAGENT; RESIN; TRITYL BROMIDE; TRITYL DERIVATIVE; UNCLASSIFIED DRUG;

EID: 50049116914     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.07.130     Document Type: Article
Times cited : (14)

References (35)
  • 8
    • 0141460600 scopus 로고    scopus 로고
    • For a recent review on anchoring of alcohols and phenols to solid supports, see:
    • For a recent review on anchoring of alcohols and phenols to solid supports, see:. Nam N.-H., Sardari S., and Parang K. J. Comb. Chem. 5 (2003) 479-546
    • (2003) J. Comb. Chem. , vol.5 , pp. 479-546
    • Nam, N.-H.1    Sardari, S.2    Parang, K.3
  • 26
    • 50049087023 scopus 로고    scopus 로고
    • note
    • 3: C, 73.82; H, 7.12; N, 4.30. Found: C, 73.91; H, 6.98; N, 4.33.
  • 27
    • 50049135995 scopus 로고    scopus 로고
    • note
    • 2. The resin was drained, washed with DMF, dioxane, MeOH, and DCM (each 3 × 5 mL for 5 min), and then cleaved with 2% TFA-DCM (2 × 2 mL for 30 min). The resin was further eluted with DCM (2 mL), and the resulting solutions were combined and co-evaporated with toluene in vacuo. The crude material was purified by preparative reversed-phase HPLC-DAD using a 21.2 × 250 mm Phenomenex C18 column (5 μm, 100 Å) in a system consisting of two preparative-scale pumps, an autosampler and a multiple-wavelength UV detector.
  • 28
    • 50049091243 scopus 로고    scopus 로고
    • note
    • 3: C, 74.28; H, 6.55; N, 4.33. Found: C, 74.68; H, 6.79; N, 4.61.
  • 29
    • 50049115619 scopus 로고    scopus 로고
    • note
    • 21 employing successive additions of DCM (1.5 mL), 0.5 M HCl in DCM (1.0 mL), water (25 μL), and triisopropylsilane (TIS, 25 μL), followed by shaking for 1 h, was tested with a resin loaded with alcohol 1b. In this case, formation of the by-product was avoided; a 95% yield of the desired compound was observed.
  • 30
    • 0034637623 scopus 로고    scopus 로고
    • For additional information concerning trifluoroacetylation of alcohols during TFA treatment, see: and references cited therein
    • For additional information concerning trifluoroacetylation of alcohols during TFA treatment, see:. Atkinson G.E., Fisher P.M., and Chan W.C. J. Org. Chem. 65 (2000) 5048-5056 and references cited therein
    • (2000) J. Org. Chem. , vol.65 , pp. 5048-5056
    • Atkinson, G.E.1    Fisher, P.M.2    Chan, W.C.3
  • 32
    • 50049113904 scopus 로고    scopus 로고
    • note
    • + 394.1437; found 394.1421; ΔM 4 ppm.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.