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Volumn , Issue 3, 2008, Pages 467-474

Acid-induced and reductive transformations of enantiopure 3,6-dihydro-2H-1,2-oxazines - Synthesis of dideoxyamino carbohydrate derivatives

Author keywords

1,2 oxazines; Carbohydrates; Furans; Pyrans; Reductions; Samarium diiodide

Indexed keywords


EID: 38849106858     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200700792     Document Type: Article
Times cited : (30)

References (43)
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    • Employing directly hydrochloric acid in methanol furnished compounds 2 and 3 in inferior yields. Probably, low concentrations of HCl are advantageous for a clean transformation.
    • Employing directly hydrochloric acid in methanol furnished compounds 2 and 3 in inferior yields. Probably, low concentrations of HCl are advantageous for a clean transformation.
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    • G. A. Olah, J. G. Shih, G. K. S. Prakash, Fluorine Containing Reagents in Organic Chemistry in Fluorine: The First Hundred Years (Eds.: R. E. Banks, D. W. A. Sharp, J. C. Tatlow), Elsevier, New York, 1992, p. 377-381;
    • b) G. A. Olah, J. G. Shih, G. K. S. Prakash, Fluorine Containing Reagents in Organic Chemistry in Fluorine: The First Hundred Years (Eds.: R. E. Banks, D. W. A. Sharp, J. C. Tatlow), Elsevier, New York, 1992, p. 377-381;
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    • In solution also only one epimer can be detected by NMR spectroscopy
    • In solution also only one epimer can be detected by NMR spectroscopy.
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    • For a non-reductive method, see
    • For a non-reductive method, see: A. Al-Harrasi, H.-U. Reißig, Synlett 2005, 1152-1154.
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    • Al-Harrasi, A.1    Reißig, H.-U.2
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    • 2, see: a) G. E. Keck, S. F. McHardy, T. T. Wager, Tetrahedron Lett. 1995, 36, 7419-7422;
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    • To the best of our knowledge, 4-amino-2,4-dideoxyhex-3-uloses have not been reported before. For a 2-deoxyhex-3-ulose, see: a T. Bando, Y. Matsushima, Bull. Chem. Soc. Jpn. 1973, 46, 593-596;
    • To the best of our knowledge, 4-amino-2,4-dideoxyhex-3-uloses have not been reported before. For a 2-deoxyhex-3-ulose, see: a) T. Bando, Y. Matsushima, Bull. Chem. Soc. Jpn. 1973, 46, 593-596;
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    • for 4-amino-4-deoxyhex-3-ulose derivatives, see: c
    • for 4-amino-4-deoxyhex-3-ulose derivatives, see: c) J. Yoshimura, M. Funabashi, Carbohydr. Res. 1969, 11, 278-281;
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    • To the best of our knowledge, 4-amino-2,4-dideoxyoct-3-uloses have not been reported before. A 4-amino-2,4-dideoxyoct-3-ulosonic acid derivative is proposed as an intermediate in a thiazole synthesis: a S. Knapp, B. Amorelli, G. A. Doss, Tetrahedron Lett. 2004, 45, 8507-8510;
    • To the best of our knowledge, 4-amino-2,4-dideoxyoct-3-uloses have not been reported before. A 4-amino-2,4-dideoxyoct-3-ulosonic acid derivative is proposed as an intermediate in a thiazole synthesis: a) S. Knapp, B. Amorelli, G. A. Doss, Tetrahedron Lett. 2004, 45, 8507-8510;
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    • for synthesis and isolation of the first naturally occurring oct-3-ulose, see: c
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    • For a deoxy sugar synthesis using lithiated alkoxyallenes, see
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    • Donor-Substituted Allenes
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.