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Volumn 64, Issue 40, 2008, Pages 9574-9580

Synthesis of five and six membered aminocyclitols: stereoselective Michael and Henry reaction approach with d-glucose derived α,β-unsaturated ester

Author keywords

Aminocyclitols; Carbohydrates; Henry reaction; Michael addition; Nitroinositol

Indexed keywords

1,2 O ISOPROPYLIDENE 3 O BENZYL 5,6 DIDEOXY 5 NITROMETHYL B IDO HEPTO 1,4 FURANOSE; 2 (BENZYLOXY) 4 (2 HYDROXYMETHYL) 5 NITROCYCLOPENTANE 1,3 DIOL; 3 (BENZYLOXY) 5 (2 CARBETHOXYMETHYL) 6 NITROCYCLOHEXANE 1,2,4 TRIOL; 3 (BENZYLOXY) 5 (2 HYDROXYETHYL) 6 NITROCYCLOHEXANE 1,2,4 TRIOL; 3 (BENZYLOXY) 5 (2 HYDROXYMETHYL) 6 NITROCYCLOHEXANE 1,2,4 TRIOL; 5 (2 ACETOXYETHYL) 2 (BENZYLOXY) 4 NITROCYCLOPENT 3 ENYL ACETATE; 5 (2 ACETOXYETHYL) 3 (BENZYLOXY) NITROCYCLOHEXANE 1,2,4 TRIYL TRIACETATE; 5 AMINO 4 (2 HYDROXYETHYL)CYCLOCYCLOPENTANE 1,2,3 TRIOL; 6 AMINO 5 (2 HYDROXYETHYL) CYCLOHEXANE 1,2,3,4 TETRAOL; AMINOCYCLITOL; ESTER DERIVATIVE; ETHYL 1,2 O ISOPROPYLIDENE 3 O BENZYL 5 NITROMETHYL 5,8 DIDEOXY B IDO HEPTOFURANURONATE; GLUCOSE; NITROMETHANE; SODIUM IODATE;

EID: 49349101882     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.07.049     Document Type: Article
Times cited : (18)

References (95)
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    • note
    • 13C NMR spectra of crude mixture showed additional signals <10%, probably due to the other diastereomer. Assuming that the additional signals are due to the other isomer, the ratio of two diastereomers is l-ido/d-gluco=92:08.
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    • note
    • The observed stereoselectivity was in accordance with that reported previously by us in the conjugate addition of substituted amines with α,β-unsaturated esters 7 and was rationalized in terms of Felkin-Anh transition states see Refs. 19,20f.
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    • The use of DABCO as a most efficient base in the Henry reaction, under microwave reaction condition, is reported by
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    • 13C NMR spectra of crude reaction mixture showed additional signals <05% probably due to the side product.
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    • note
    • 2 functionality is compatible under LAH condition see Ref. 1.
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    • note
    • The crystallographic data have been deposited with the Cambridge Crystallographic Data Centre as deposition nos. CCDC-685631 (8) and CCDC-685632 (11). Copies of the data can be obtained, free of charge, on application to the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44 1223 336033; e-mail: deposit@ccdc.cam.ac.uk].


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.