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Di Nardo, C.; Varela, O.; de Lederkremer, R.M.; Baggio, R.F.; Vega, D.R.; Garland, M.T. "Bromination of sugar enones and enonolactones" (1995) Carbohydrate Research. 269(1):99-109
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Abstract:

Bromination of 2,4,6-tri-O-benzoyl-3-deoxy-d-erytro-hex-2-enono-1,5-lactone (1) took place diastereoselectively to afford a single product: 2,4,6-tri-O-benzoyl-2,3-dibromo-3-deoxy-d-altrono-1,5-lactone (2). The configuration of C-2 and C-3 was determined as R,R by NMR spectroscopy and taking into account considerations of the stereochemical course of the bromination. The configuration of 2 was confirmed by X-ray analysis, which also revealed that the conformation of the lactone ring consists of a 4H3(d) distorted half-chair. The bromine addition to 2,5,6,7-tetra-O-benzoyl-d-arabino-hept-2-enono-1,4-lactone (5), readily prepared by DBU-promoted elimination from the perbenzoylated lactone derivative 4, was also diastereoselective and led to the dibromo derivative 6, whose configuration for C-2 and C-3 was assigned as S,S. Bromination of the α,β-unsaturated carbonyl system of 2-propyl 6-O-acetyl-3,4-dideoxy-α-d-glycero-hex-3-enopyranosid-2-ulose (7) afforded an unsaturated monobromo derivative: 2-propyl 6-O-acetyl-3-bromo-3,4-dideoxy-α-d-glycero-hex-3-enopyranosid-2-ulose (8), suggesting that dehydrobromination occurred after addition of bromine. © 1995.

Registro:

Documento: Artículo
Título:Bromination of sugar enones and enonolactones
Autor:Di Nardo, C.; Varela, O.; de Lederkremer, R.M.; Baggio, R.F.; Vega, D.R.; Garland, M.T.
Filiación:Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellon II, Ciudad Universitaria, 1428 Buenos Aires, Argentina
División Física del Sólido, Departamento de Física, Comisión Nacional de Energía Atómica, Buenos Aires, Argentina
Departamento de Física, Facultad de Ciencias Físicas y Matemáticas, Universidad de Chile, Santiago de Chile, Chile
Palabras clave:Bromination; Enones; Enonolactones; Sugar enones and enonolactones; carbohydrate derivative; organobromine derivative; article; bromination; nuclear magnetic resonance; priority journal; reaction analysis; stereochemistry; X ray diffraction
Año:1995
Volumen:269
Número:1
Página de inicio:99
Página de fin:109
DOI: http://dx.doi.org/10.1016/0008-6215(94)00352-G
Título revista:Carbohydrate Research
Título revista abreviado:Carbohydr. Res.
ISSN:00086215
CODEN:CRBRA
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v269_n1_p99_DiNardo

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Citas:

---------- APA ----------
Di Nardo, C., Varela, O., de Lederkremer, R.M., Baggio, R.F., Vega, D.R. & Garland, M.T. (1995) . Bromination of sugar enones and enonolactones. Carbohydrate Research, 269(1), 99-109.
http://dx.doi.org/10.1016/0008-6215(94)00352-G
---------- CHICAGO ----------
Di Nardo, C., Varela, O., de Lederkremer, R.M., Baggio, R.F., Vega, D.R., Garland, M.T. "Bromination of sugar enones and enonolactones" . Carbohydrate Research 269, no. 1 (1995) : 99-109.
http://dx.doi.org/10.1016/0008-6215(94)00352-G
---------- MLA ----------
Di Nardo, C., Varela, O., de Lederkremer, R.M., Baggio, R.F., Vega, D.R., Garland, M.T. "Bromination of sugar enones and enonolactones" . Carbohydrate Research, vol. 269, no. 1, 1995, pp. 99-109.
http://dx.doi.org/10.1016/0008-6215(94)00352-G
---------- VANCOUVER ----------
Di Nardo, C., Varela, O., de Lederkremer, R.M., Baggio, R.F., Vega, D.R., Garland, M.T. Bromination of sugar enones and enonolactones. Carbohydr. Res. 1995;269(1):99-109.
http://dx.doi.org/10.1016/0008-6215(94)00352-G