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Volumn 20, Issue 3, 2009, Pages 305-312

A practical synthesis of (2R)-3,5-di-O-benzoyl-2-fluoro-2-C-methyl-d-ribono-γ-lactone

Author keywords

[No Author keywords available]

Indexed keywords

3,5 DI O BENZOYL 2 FLUORO 2 C METHYL DEXTRO RIBONO GAMMA LACTONE; ETHYL 4,5 ISOPROPYLIDENE 2 FLUORO 3 HYDROXY 2 METHYLVALERATE; ETHYL 4,5 ISOPROPYLIDENE 2 FLUORO 3 KETO 2 METHYLVALERATE; ETHYL 4,5 O ISOPROPYLIDENE 2 FLUORO 3 HYDROXY 2 METHYLVALERATE; LACTONE DERIVATIVE; UNCLASSIFIED DRUG; VALERIC ACID DERIVATIVE;

EID: 62849109318     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2009.02.006     Document Type: Article
Times cited : (11)

References (51)
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    • note
    • To simplify this discussion, the term 'Z' or 'E' describes only the relationship between the methyl group and metallated oxygen, and the influence of the heavier fluorine and sulfur atoms on the nomenclature is ignored.
  • 36
    • 62849128517 scopus 로고    scopus 로고
    • note
    • 3): δ 169.6, 169.4, 150.6, 142.8, 127.2, 125.9, 125.2, 116.0, 110.2, 86.7, 85.2, 18.1, 17.9.
  • 38
    • 62849121213 scopus 로고    scopus 로고
    • Prepared following the literature procedure in Ref. 11
    • Prepared following the literature procedure in Ref. 11
  • 39
    • 62849118202 scopus 로고    scopus 로고
    • Prepared following the literature procedure in Ref. 12c.
    • Prepared following the literature procedure in Ref. 12c.
  • 40
    • 62849107935 scopus 로고    scopus 로고
    • Prepared following the literature procedure in Ref. 9
    • Prepared following the literature procedure in Ref. 9
  • 41
    • 62849126222 scopus 로고    scopus 로고
    • One possible cause for the low observed stereoselectivity in these reactions could be the formation of higher percentage of E-enolate favored by fluorine-metal interactions. Although fluorine-metal interactions were detected under certain circumstances e.g, Takemura, H, Kon, N, Kotoku, M, Nakashima, S, Otsuka, K, Yasutake, M, Shimyozu, T, Inazu, T. J. Org. Chem. 2001, 66, 2778; Barr, D, Hutton, K. B, Morris, J. H, Mulvey, R. E, Reed, D, Snaith, R. J. Chem. Soc, Chem. Commun. 1986, 127; Plenio, H. ChemBioChem 2004, 5, 650; and the references cited in these papers, no strong evidence for the existence of such interactions in α-fluoroenolates were reported in the literature. Some literature results might have indicated the lack of such interaction or the lack of influence of such an interaction on the E/Z ratio of enolates. For instance, 19F NMR of the enolates of N,N-dimethylfluoroacetamide indicated an almost 1:1 mixture of E/Z isomers even at -85 °C
    • 19F NMR of the enolates of N,N-dimethylfluoroacetamide indicated an almost 1:1 mixture of E/Z isomers even at -85 °C (Welch, J. T.; Eswarakrishnan, S. J. Org. Chem. 1985, 50, 5403). Another example is that enolates 23 and 24 existed almost exclusively as Z-enolates under the reaction conditions (Refs. 15 and 17), indicating that the coordination between F-Li or F-Ti (if it exists) has little effect on the E/Z ratio.
  • 43
    • 62849092085 scopus 로고    scopus 로고
    • note
    • 3): δ 4.98 (dq, J = 61, 8.5 Hz, 1H), 4.18 (t, J = 8.5 Hz, 2H), 1.70-1.60 (m, 2H), 1.57 (dd, J = 29.5, 8.5 Hz, 3H), 1.44-1.34 (m, 2H), 0.93 (t, J = 9 Hz, 3H).
  • 44
    • 62849122701 scopus 로고    scopus 로고
    • note
    • 3): δ 170.27, 170.09, 86.45, 85.00, 72.34, 37.93, 37.91, 19.92, 19.87, 18.61, 18.59, 18.47, 18.44, 18.29, 18.26, 13.83.
  • 45
    • 62849124867 scopus 로고    scopus 로고
    • note
    • 3): δ 170.51, 170.32, 86.43, 84.99, 78.21, 26.46, 26.42, 18.58, 18.40, 9.53.
  • 51
    • 62849091124 scopus 로고    scopus 로고
    • CALB was a technical solution from BioCatalytics, Cat# SO L-101, Lot# CN02100.
    • CALB was a technical solution from BioCatalytics, Cat# SO L-101, Lot# CN02100.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.