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Abstract:

Trans-opening of the 2,3-anhydro-6-deoxy-4-O-methyl-α-D-allopyranoside with lithium bromide yields the altro and gluco regioisomers methyl 2-bromo- 2,6-dideoxy-4-O-methyl-α-D-altropyranoside and methyl 2-bromo-3,6-dideoxy- 4-O-methyl-α-D-glycopyranoside which can be hydrolysed to give the sugar precursors 2-bromo-2,6-dideoxy-4-O-methyl-α/β-D-altropyranose and 3-bromo- 3,6-dideoxy-4-O-methyl-D-glucopyranose. Under Mitsunobu conditions the altro compound yields the first 1,3-anhydro-altrose derivative. In case of the gluco derivative alkaline treatment does not give a 1,3-anhydro-glucose derivative but the 2,6-dideoxy-altrose via intermediate 2,3-epoxide formation. Methanolysis and reductive debromination under photolytic initiation were studied.

Registro:

Documento: Artículo
Título:Synthesis of thromboxane A2 models from glucose
Autor:Cirelli, A.F.; Mohn, H.; Thiem, J.
Filiación:Depto. de Quimica Orgánica, Ciudad Universitaria, Universidad de Buenos Aires, 1428 Buenos Aires, Argentina
Organisch-Chemisches Institut, Westfälische Wilhelms-Univ., Orléansring 23, D-48149 Münster, Germany
Institut für Organische Chemie, Universität Hamburg, Martin-Luther-King-Platz 6, D-20146 Hamburg, Germany
Palabras clave:1.3-Anhydro-α-D-altropyranoside; 2,6- dideoxy; 2.6-Dioxabicyclo[3.1.1]heptanes; Model compounds; Thromboxane; glucose; pyranoside; sugar; thromboxane a2; article; debromination; isomer; photolysis; priority journal; reaction analysis; synthesis
Año:1997
Volumen:303
Número:4
Página de inicio:417
Página de fin:422
DOI: http://dx.doi.org/10.1016/S0008-6215(97)00183-3
Título revista:Carbohydrate Research
Título revista abreviado:CARBOHYDR. RES.
ISSN:00086215
CODEN:CRBRA
CAS:glucose, 50-99-7, 84778-64-3; thromboxane A2, 57576-52-0
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v303_n4_p417_Cirelli

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Citas:

---------- APA ----------
Cirelli, A.F., Mohn, H. & Thiem, J. (1997) . Synthesis of thromboxane A2 models from glucose. Carbohydrate Research, 303(4), 417-422.
http://dx.doi.org/10.1016/S0008-6215(97)00183-3
---------- CHICAGO ----------
Cirelli, A.F., Mohn, H., Thiem, J. "Synthesis of thromboxane A2 models from glucose" . Carbohydrate Research 303, no. 4 (1997) : 417-422.
http://dx.doi.org/10.1016/S0008-6215(97)00183-3
---------- MLA ----------
Cirelli, A.F., Mohn, H., Thiem, J. "Synthesis of thromboxane A2 models from glucose" . Carbohydrate Research, vol. 303, no. 4, 1997, pp. 417-422.
http://dx.doi.org/10.1016/S0008-6215(97)00183-3
---------- VANCOUVER ----------
Cirelli, A.F., Mohn, H., Thiem, J. Synthesis of thromboxane A2 models from glucose. CARBOHYDR. RES. 1997;303(4):417-422.
http://dx.doi.org/10.1016/S0008-6215(97)00183-3