Stereoselective synthesis of azasugars by electrochemical oxidation

Tetrahedron Letters

Volumn 45, Issue 44, 2004, Pages 8177-8181

  Furukubo, Shigeru ^a   Moriyama, Noriaki ^a   Onomura, Osamu ^a   Matsumura, Yoshihiro ^a  

^a NAGASAKI UNIVERSITY   (Japan)

Author keywords

Acetoxylation; Azasugar; Electrochemical oxidation; Stereoselective

Indexed keywords

PIPERIDINE DERIVATIVE; SUGAR;

ARTICLE; BROMINATION; DRUG SYNTHESIS; ELECTROCHEMISTRY; ELIMINATION REACTION; OXIDATION KINETICS; REDUCTION KINETICS; STEREOCHEMISTRY; STEREOISOMERISM; X RAY ANALYSIS;

EID: 4744362145     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.09.036     Document Type: Article

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23. 4 and the solvent was removed in vacuo, the residue was subjected on chromatography (silica gel) (AcOEt:n-hexane = 1:3) to afford 1,2,3-triacetoxy-5S-acetoxymethyl-N-methoxycarbonyl piperidine (5) in 85% yield
24. Determined by HPLC method; YMC-Pack SIL (0.46 cm∅ × 15 cm), n-hexane/ethanol = 10/1, wavelength: 210 nm, flow rate: 0.5 mL/min, retention time of major isomer: 11.4 min
25. 3)
26. 2S,3S and 21 were mounted on a glass fiber. All measurements were made on a Quantum CCD area detector coupled with a Rigaku AFC7 diffractometer using graphite-monochromated Mo Kα radiation (λ = 0.71069 Å) at 296-297 K. Data were collected in 0.50° oscillations with 30.0 s exposures. A sweep of data was done using φ oscillations from 0.0° to 190.0° at χ = 0° and a second sweep was performed using w oscillations between -19.0° and 23.0° at χ = 90.0°. The crystal-to-detector distance was 40.7 mm, and the detector swing angle was -5.0°. The data were corrected for Lorentz and polarization effects. The structures were solved by direct methods (SIR92) and refined by full matrix least squares methods. All calculations were performed using TEXSAN. CCDC 246337 & 246338 contains the supplementary crystallographic data for this paper. The data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, by e-mailing data_request@ccdc.cam.ac. uk, or by contacting The Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: +44(0)-1223-336033
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29. 3)
30. The stereoselectivity can be also explainable in terms of a participating effect of 3-acetoxyl group or thermodynamic control of the products
31. A mechanism involving an initial attack of acetic acid on C-2 of a cation (C-2) radical (C-1) intermediate cannot be denied