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Abstract:

Acetylation of 2-amino-2-deoxy-d-gluconic acid (1) with acetyl chloride-pyridine gave 2,3-unsaturated six- and five-membered lactones (2 and 3). Their benzoylated analogs (4 and 5) were obtained by benzoylation of 1 with benzoyl chloride-pyridine. Reaction of 1 with hot acetic anhydride-sodium acetate gave a ∼1:2 mixture of (E)- and (Z)-2-acetamido-6-acetoxyhexa-2,4-dien-4-olide (6-E and 6-Z). Treatment of 3 with 1,8-diazabicyclo[5.4.0]undec-7-ene also gave as the main product 6-Z, which was isolated crystalline from the reaction mixture. The same reaction applied to compound 5 gave selectively the Z-isomer of the benzoylated furanone 7. Partial and total hydrogenation (H2PdC) of the mixture 6-E,Z gave, respectively, a racemic monounsaturated lactone (8) and a dideoxy lactone (9), for which the threo-configuration for the chiral centers at C-2 and C-4 was determined. Acidic removal of the acetyl groups from 9 afforded the 2-amino-6-hydroxy-1,4-lactone hydrochloride 10. On the other hand, acetylation at high temperature of the 4,6-O-benzylidene derivative of 1 (11) gave the 2,3-unsaturated, six-membered lactone (12), precursor of 2-acetamido-6-acetoxyhexa-2,4-dien-5-olide (14). © 1989.

Registro:

Documento: Artículo
Título:Confirmation of the structures of the products obtained on acylation of 2-amino-2-deoxy-d-gluconic acid
Autor:Horton, D.; Thomson, J.K.; Varela, O.; Nin, A.; de Lederkremer, R.M.
Filiación:Department of Chemistry, The Ohio State University, Columbus, OH 43210, United States
Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellon II, 1428 Buenos Aires, Argentina
Palabras clave:benzenecarbonyl chloride; benzoic acid derivative; drug derivative; glucosamine; glucosaminic acid; lactone; acetylation; article; chemical structure; nuclear magnetic resonance spectroscopy; stereoisomerism; synthesis; Acetylation; Benzoates; Glucosamine; Lactones; Magnetic Resonance Spectroscopy; Molecular Structure; Stereoisomerism; Support, Non-U.S. Gov't; Support, U.S. Gov't, P.H.S.
Año:1989
Volumen:193
Número:C
Página de inicio:49
Página de fin:60
DOI: http://dx.doi.org/10.1016/0008-6215(89)85106-7
Título revista:Carbohydrate Research
Título revista abreviado:Carbohydr. Res.
ISSN:00086215
CODEN:CRBRA
CAS:Benzoates; benzoyl chloride, 98-88-4; Glucosamine, 3416-24-8; glucosaminic acid, 6165-14-6; Lactones
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v193_nC_p49_Horton

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Citas:

---------- APA ----------
Horton, D., Thomson, J.K., Varela, O., Nin, A. & de Lederkremer, R.M. (1989) . Confirmation of the structures of the products obtained on acylation of 2-amino-2-deoxy-d-gluconic acid. Carbohydrate Research, 193(C), 49-60.
http://dx.doi.org/10.1016/0008-6215(89)85106-7
---------- CHICAGO ----------
Horton, D., Thomson, J.K., Varela, O., Nin, A., de Lederkremer, R.M. "Confirmation of the structures of the products obtained on acylation of 2-amino-2-deoxy-d-gluconic acid" . Carbohydrate Research 193, no. C (1989) : 49-60.
http://dx.doi.org/10.1016/0008-6215(89)85106-7
---------- MLA ----------
Horton, D., Thomson, J.K., Varela, O., Nin, A., de Lederkremer, R.M. "Confirmation of the structures of the products obtained on acylation of 2-amino-2-deoxy-d-gluconic acid" . Carbohydrate Research, vol. 193, no. C, 1989, pp. 49-60.
http://dx.doi.org/10.1016/0008-6215(89)85106-7
---------- VANCOUVER ----------
Horton, D., Thomson, J.K., Varela, O., Nin, A., de Lederkremer, R.M. Confirmation of the structures of the products obtained on acylation of 2-amino-2-deoxy-d-gluconic acid. Carbohydr. Res. 1989;193(C):49-60.
http://dx.doi.org/10.1016/0008-6215(89)85106-7