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Abstract:

A convenient synthesis of enantiomerically pure aldopentono-1,4-thiolactones is described. Thus, 4-thio-d-ribono-1,4-lactone (12) has been prepared from D-gulono-1,4-lactone (1), via its 2,3-O-isopropylidene derivative 3. The 5,6-glycol system of 3 was oxidized with NaIO4. Chemoselective reduction of the resulting aldehyde function with NaBH3CN led to 2,3-O-isopropylidene-l-lyxono-1,4-lactone (7). Tosylation of 7 and subsequent treatment of the tosylate 8 with sodium methoxide afforded methyl 4,5-epoxy-2,3-O-isopropylidene-l-lyxonate (9) as a key intermediate. Treatment of 9 with thiourea gave the 4,5-thiirane derivative having the d-ribo configuration (10). Regioselective opening of the thiirane ring and simultaneous thiolactonization took place by heating 10 with KOAc-HOAc-DMF. The resulting 5-O-acetyl-2,3-O-isopropylidene-4-thio-d-ribono-1,4-lactone (11) was readily converted, by acid removal (2% HCl) of the protecting groups, into the crystalline thiolactone 12. A similar approach was employed for the synthesis of 4-thio-l-lyxono-1,4-lactone (19), starting from d-ribono-1,4-lactone (13). © 1993, American Chemical Society. All rights reserved.

Registro:

Documento: Artículo
Título:First Synthesis of Aldopentono-1,4-thiolactones
Autor:Varela, O.; Zunszain, P.A.
Filiación:Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón II, 1428, Buenos Aires, Argentina
Año:1993
Volumen:58
Número:27
Página de inicio:7860
Página de fin:7864
DOI: http://dx.doi.org/10.1021/jo00079a034
Título revista:Journal of Organic Chemistry
Título revista abreviado:J. Org. Chem.
ISSN:00223263
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223263_v58_n27_p7860_Varela

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Citas:

---------- APA ----------
Varela, O. & Zunszain, P.A. (1993) . First Synthesis of Aldopentono-1,4-thiolactones. Journal of Organic Chemistry, 58(27), 7860-7864.
http://dx.doi.org/10.1021/jo00079a034
---------- CHICAGO ----------
Varela, O., Zunszain, P.A. "First Synthesis of Aldopentono-1,4-thiolactones" . Journal of Organic Chemistry 58, no. 27 (1993) : 7860-7864.
http://dx.doi.org/10.1021/jo00079a034
---------- MLA ----------
Varela, O., Zunszain, P.A. "First Synthesis of Aldopentono-1,4-thiolactones" . Journal of Organic Chemistry, vol. 58, no. 27, 1993, pp. 7860-7864.
http://dx.doi.org/10.1021/jo00079a034
---------- VANCOUVER ----------
Varela, O., Zunszain, P.A. First Synthesis of Aldopentono-1,4-thiolactones. J. Org. Chem. 1993;58(27):7860-7864.
http://dx.doi.org/10.1021/jo00079a034