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Volumn 100, Issue 12, 2000, Pages 4395-4421

Methods for anomeric carbon-linked and fused sugar amino acid synthesis: the gateway to artificial glycopeptides

Author keywords

[No Author keywords available]

Indexed keywords

ATOMS; CARBON; CHEMICAL BONDS; CONDENSATION; DRUG PRODUCTS; HYDROLYSIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLEFINS; PROTEINS; SUGARS; SYNTHESIS (CHEMICAL);

EID: 0034507032     PISSN: 00092665     EISSN: None     Source Type: Journal    
DOI: 10.1021/cr9903003     Document Type: Article
Times cited : (307)

References (149)
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    • 4 to the carboxylic acid group. For a collection of references, see ref 25.
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    • note
    • No evidence is provided for the structure of compounds 60-63. However, the above stereochemical assignments are in agreement with the main stereochemical course of radical C-glycosylation reactions reported in the literature and with parallel studies of radical additions to methyleneoxazolidinones that were underway in the authors laboratory.
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    • 4) and carbon-carbon double bond (diimide), and finally Barton-McCombie dehydroxylation.
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    • Various zinc reagents for this and related methodologies were prepared in both the Gallagher and Jackson laboratories, see: refs 48 and 67. See also: (a) Jackson, R. F. W.; Wishart, N.; Wood, A.; James, K.; Wythes, M. J. J. Org. Chem. 1992, 57, 3397.
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    • This reaction has been applied to various sugar lactones and constitutes the initial step of the thiazole-based synthesis of formyl C-glycosides, see ref 29
    • This reaction has been applied to various sugar lactones and constitutes the initial step of the thiazole-based synthesis of formyl C-glycosides, see ref 29.
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    • note
    • Other examples of this synthetic route by the use of benzothiazole as the formyl group equivalent have been demonstrated in the authors laboratory. The use of the benzothiazole ring avoids some side reactions that have been occasionally observed between the azido group and the intermediates that are formed in the unmasking sequence of the thiazole ring to the formyl group.
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    • Numerous spyrohydantoins of carbohydrates have been also prepared by methods which do not involve fused anomeric glycines as precursors. Instead, anomeric azido-amides and bromo-amides have been employed. For selected examples and leading references, see: (a) Mio, S.; Kumagawa, Y.; Sugai, S. Tetrahedron 1991, 47, 2133.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.