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Abstract:

Both thiosemicarbazone groups of the derivative 1 of 3-deoxy-D-erythro-hexos-2-ulose underwent, on acetylation, a heterocyclization process to give (5R,5′R)-2,2′-diacetamido-4,4′-di-N-acetyl-5′-(1- deoxy-2,3,4-tri-O-acetyl-D-erythritol-1-yl)-5,5′-bis(1,3,4- thiadiazoline) (2) as a major product. The X-ray diffraction data of a single crystal of 2 indicated the R,R configuration for the stereocenters of the thiadiazoline rings (C-5 and C-5′). In the solid state, 2 adopts a sickle conformation (by clockwise rotation of the C-2-C-3 axis of the sugar chain) which has a S//O 1,3-parallel interaction. In solution, as determined by 1H NMR spectroscopy which included NOE experiments, a similar sickle conformation was observed. From the reaction mixture of acetylation of 1 was isolated the bis(thiadiazoline) 3 as a by-product . The configuration of the C-5 and C-5′ stereocenters of 3 were respectively assigned as S,R by comparison of the physical and spectroscopic data of this compound with those of 2. © 2002 Elsevier Science Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Heterocyclization of 3-deoxy-D-erythro-hexos-2-ulose-1,2-bis(thiosemicarbazone). Crystal structure of the major diastereomer
Autor:Martins Alho, M.A.; Baggio, R.; Garland, M.T.; D'Accorso, N.B.; Varela, O.
Filiación:CIHIDECAR (CONICET), Departamento De Química Orgánica, Ciudad Universitaria, 3o Piso, Pabellón II, 1428 Buenos Aires, Argentina
Departamento De Física, Comisión Nacional De Energía Atómica, Avda. del Libertador 8250, 1429 Buenos Aires, Argentina
Departamento De Física, Facultad De Ciencias Físicas Y Matemáticas, Univ. De Chile Y Ctro. para La Invest. Interdisciplinaria Avanzada En Ciencia De Los Materiales, Avda. Blanco Encalada 2008, Casilla 487-3 Santiago, Chile
Palabras clave:Heterocyclization; Sugar thiosemicarbazone; Thiadiazoline; X-ray diffraction; Acetylation; Crystals; Data acquisition; Nuclear magnetic resonance; Spectroscopy; X ray diffraction analysis; Heterocyclization; Carbohydrates; 2,2' diacetamido 4,4' di n acetyl 5' (1 deoxy 2,3,4 tri o acetyl dextro erythritol 1 yl) 5,5' bis(1,3,4 thiadiazoline); 3 deoxy dextro erythro hexos 2 ulose 1,2 bis(thiosemicarbazone); sugar; thiadiazole derivative; thiosemicarbazone derivative; unclassified drug; 3 deoxy D erythro hexos 2 ulose 1,2 bis(thiosemicarbazone); 3-deoxy-D-erythro-hexos-2-ulose-1,2-bis(thiosemicarbazone); ketose; thiosemicarbazone derivative; article; crystal structure; diastereoisomer; drug acetylation; drug structure; priority journal; proton nuclear magnetic resonance; stereochemistry; structure analysis; X ray diffraction; chemical structure; chemistry; conformation; crystallization; cyclization; stereoisomerism; Carbohydrate Conformation; Crystallization; Cyclization; Ketoses; Models, Molecular; Stereoisomerism; Thiosemicarbazones; X-Ray Diffraction
Año:2002
Volumen:337
Número:15
Página de inicio:1397
Página de fin:1403
DOI: http://dx.doi.org/10.1016/S0008-6215(02)00157-X
Título revista:Carbohydrate Research
Título revista abreviado:Carbohydr. Res.
ISSN:00086215
CODEN:CRBRA
CAS:3-deoxy-D-erythro-hexos-2-ulose-1,2-bis(thiosemicarbazone); Ketoses; Thiosemicarbazones
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v337_n15_p1397_MartinsAlho

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Citas:

---------- APA ----------
Martins Alho, M.A., Baggio, R., Garland, M.T., D'Accorso, N.B. & Varela, O. (2002) . Heterocyclization of 3-deoxy-D-erythro-hexos-2-ulose-1,2-bis(thiosemicarbazone). Crystal structure of the major diastereomer. Carbohydrate Research, 337(15), 1397-1403.
http://dx.doi.org/10.1016/S0008-6215(02)00157-X
---------- CHICAGO ----------
Martins Alho, M.A., Baggio, R., Garland, M.T., D'Accorso, N.B., Varela, O. "Heterocyclization of 3-deoxy-D-erythro-hexos-2-ulose-1,2-bis(thiosemicarbazone). Crystal structure of the major diastereomer" . Carbohydrate Research 337, no. 15 (2002) : 1397-1403.
http://dx.doi.org/10.1016/S0008-6215(02)00157-X
---------- MLA ----------
Martins Alho, M.A., Baggio, R., Garland, M.T., D'Accorso, N.B., Varela, O. "Heterocyclization of 3-deoxy-D-erythro-hexos-2-ulose-1,2-bis(thiosemicarbazone). Crystal structure of the major diastereomer" . Carbohydrate Research, vol. 337, no. 15, 2002, pp. 1397-1403.
http://dx.doi.org/10.1016/S0008-6215(02)00157-X
---------- VANCOUVER ----------
Martins Alho, M.A., Baggio, R., Garland, M.T., D'Accorso, N.B., Varela, O. Heterocyclization of 3-deoxy-D-erythro-hexos-2-ulose-1,2-bis(thiosemicarbazone). Crystal structure of the major diastereomer. Carbohydr. Res. 2002;337(15):1397-1403.
http://dx.doi.org/10.1016/S0008-6215(02)00157-X