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Volumn 44, Issue 33, 2003, Pages 6347-6350

Fragmentation of carbohydrate anomeric alkoxy radicals: A new synthesis of chiral 1-halo-1-bromo compounds

Author keywords

[No Author keywords available]

Indexed keywords

ALDITOL; BENZENE DERIVATIVE; BROMINE; BROMINE DERIVATIVE; CARBOHYDRATE DERIVATIVE; RADICAL;

EID: 18744413702     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01399-6     Document Type: Article
Times cited : (21)

References (39)
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    • For recent illustrative examples, see: (a) Xi, H.; Gibb, C. L. D.; Gibb, B. C. J. Org. Chem. 1999, 64, 9286-9288; (b) Cambie, R. C.; Rickard, C. E. F.; Starnge, G. A. Aust. J. Chem. 1997, 50, 841-848; (c) Hoffmann, R. W.; Bovicelli, P. Synthesis 1990, 657-659; (d) Takeda, T.; Sasaki, R.; Nakamura, A.; Yamauchi, S.; Fujiwara, T. Synlett 1996, 273-274; Takeda, T.; Sasaki, R.; Yamauchi, S.; Fujiwara, T. Tetrahedron 1997, 53, 557-566; (e) Larock, R. C.; Leong, W. W. In Comprehensive Organic Synthesis; Trost, B.; Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 4, pp. 279-287; (f) Onishi, T.; Otake, Y.; Hirose, N.; Nakano, T.; Torii, T.; Nakazawa, M.; Izawa, K. Tetrahedron Lett. 2001, 42, 6337-6340; (g) Martínez, A. G.; Fernández, A. H.; Alvarez, R. M.; Fraile, A. G.; Calderón, J. B.; Barcina, J. O. Synthesis 1986, 1076-1078.
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    • For the synthesis of the analogous (5S,6R)-5-acetoxy-6-(acetoxymethyl)-3-iodo-5,6-dihydro-2H-pyran-2-one using other methodology, see:
    • For the synthesis of the analogous (5S,6R)-5-acetoxy-6-(acetoxymethyl)-3-iodo-5,6-dihydro-2H-pyran-2-one using other methodology, see: Evans R.D., Schauble J.H. Synthesis. 1986;727-730.
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    • 8: C, 32.17; H, 3.60. Found: C, 32.51; H, 3.31
    • 8: C, 32.17; H, 3.60. Found: C, 32.51; H, 3.31.
  • 30
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    • As determined by NMR spectroscopy the halohydrins were diastereoisomeric mixtures in most cases (see: Ref. 14). Chromatographically homogeneous products with correct elemental analyses were used in the fragmentation reactions.
    • As determined by NMR spectroscopy the halohydrins were diastereoisomeric mixtures in most cases (see: Ref. 14). Chromatographically homogeneous products with correct elemental analyses were used in the fragmentation reactions.
  • 36
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    • note
    • 2. The organic layer was washed with 10% aqueous sodium thiosulfate, dried and concentrated in vacuo. Chromatotron chromatography of the residue (n-hexane-EtOAc mixtures) afforded the required halo-bromine compound. Under these conditions formation of the pyranone byproducts apparently does not appear to occur to an appreciable extent. The reaction was performed under dilute conditions to avoid a high concentration of bromine but this aspect has not been optimized.
  • 37
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    • For the synthesis of 2-deoxy-hex-1-enitols (glycals), see:
    • For the synthesis of 2-deoxy-hex-1-enitols (glycals), see: Shull B.K., Wu Z., Koreeda M. J. Carbohydr. Chem. 15:1996;955-964.
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    • Shull, B.K.1    Wu, Z.2    Koreeda, M.3
  • 38
    • 85031144993 scopus 로고    scopus 로고
    • note
    • 6: C, 30.80; H, 3.62. Found: C, 30.94; H, 3.66.
  • 39
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    • note
    • 16: C, 39.15; H, 4.38. Found: C, 39.14; H, 4.10.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.