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Volumn 7, Issue 22, 2001, Pages 4772-4789

The total synthesis of c-glycosides with completely resolved seven-carbon backbone polyol stereochemistry: Stereochemical correlations and access to L-configured and other rare carbohydrates

Author keywords

C glycosides; Carbohydrates; Cycloaddition; De novo syntheses; Stereochemical coalescence

Indexed keywords

ALCOHOLS; BIOSYNTHESIS; HYDROXYLATION; REDUCTION; STEREOCHEMISTRY; SUGARS;

EID: 0000652935     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20011119)7:22<4771::aid-chem4771>3.3.co;2-a     Document Type: Article
Times cited : (29)

References (125)
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    • In conventional carbohydrate nomenclature the prefix DL denotes a racemate; see: http://www.chem.qmw.ac.uk/iupac/2carb. Regarding the nomenclature of C-glycosides, see also ref. [7a], Chapter 1.
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    • d) for a survey on per-O-benzylated C-glycosides with β-D-gluco configuration and applications in combinatorial synthesis, see: O. Lockhoff, Angew. Chem. 1998, 110, 3634;
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    • Enantioselective deprotonation of 11 was achieved by using nBuLi and (+)-bis[(R)-1-phenylethyl]amine to form the chiral lithium amide base. See: a) N. S. Simpkins, P. J. Cox, Tetrahedron: Asymmetry 1991, 2, 1;
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    • PhD thesis, University of Hannover, (Chemical Equation Presented)
    • The enantiomeric starting material (+)-12 led to enantiomeric C-glycosides 5 and 6 in protected form (Scheme 12): For an application in β-C-mannoside synthesis: R. Dunkel, PhD thesis, University of Hannover, 1999. (Chemical Equation Presented)
    • (1999)
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    • PhD thesis, University of Hannover, R. Wartchow, M. Mentzel, H. Reuter, H. M. R. Hoffmann, CCDC-165882, Cambridge
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    • note
    • This strategy was used to synthesize the spongistatin F-segment which contains a tetrahydropyran ring with five all-equatorial substituents: see ref. [22b].
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    • see also ref. [28b]
    • c) see also ref. [28b].
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    • glycosyl donors with α-oxyanion reactivity: R. Dunkel, H. M. R. Hoffmann, Tetrahedron 1999, 55, 3385, and references therein.
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    • definitive stereochemical elucidation: b) T. F. Molinski, Tetrahedron Lett. 1996, 37, 7879.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.