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Sznaidman, M.L.; Cirelli, A.F.; de Lederkremer, R.M. "Synthesis of 5-O-methyl-d-galactofuranose" (1986) Carbohydrate Research. 146(2):233-240
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Abstract:

5-O-Methyl-d-galactofuranose (7) was synthesized, for the first time, in five steps from d-galactono-1,4-lactone (1) in good overall yield. Tritylation and further acetylation of 1 gave 2,3,5-tri-O-acetyl-6-O-trityl-d-galactono-1,4-lactone (2); prolonged acetylation caused elimination to form 2,5-di-O-acetyl-3-deoxy-6-O-trityl-d-threo-hex-2-enono-1,4-lactone. Detritylation of 2 with BF3 · Et2O occurred with acetyl migration and afforded 2,3,6-tri-O-acetyl-d-galactono-1,4-lactone (4). Methylation of 4 with CH2N2BF3 · Et2O gave 5-O-methyl-2,3,6-tri-O-acetyl-d-galactono-1,4-lactone. Subsequent reduction by disiamylborane followed by controlled deacetylation gave crystalline 7. The 1H- and 13C-n.m.r. spectra of 7 indicated a 1:1.3 ratio of the α and β furanose anomers. © 1986.

Registro:

Documento: Artículo
Título:Synthesis of 5-O-methyl-d-galactofuranose
Autor:Sznaidman, M.L.; Cirelli, A.F.; de Lederkremer, R.M.
Filiación:Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellon II, 1428 Buenos Aires, Argentina
Año:1986
Volumen:146
Número:2
Página de inicio:233
Página de fin:240
DOI: http://dx.doi.org/10.1016/0008-6215(86)85042-X
Título revista:Carbohydrate Research
Título revista abreviado:Carbohydr. Res.
ISSN:00086215
CODEN:CRBRA
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v146_n2_p233_Sznaidman

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Citas:

---------- APA ----------
Sznaidman, M.L., Cirelli, A.F. & de Lederkremer, R.M. (1986) . Synthesis of 5-O-methyl-d-galactofuranose. Carbohydrate Research, 146(2), 233-240.
http://dx.doi.org/10.1016/0008-6215(86)85042-X
---------- CHICAGO ----------
Sznaidman, M.L., Cirelli, A.F., de Lederkremer, R.M. "Synthesis of 5-O-methyl-d-galactofuranose" . Carbohydrate Research 146, no. 2 (1986) : 233-240.
http://dx.doi.org/10.1016/0008-6215(86)85042-X
---------- MLA ----------
Sznaidman, M.L., Cirelli, A.F., de Lederkremer, R.M. "Synthesis of 5-O-methyl-d-galactofuranose" . Carbohydrate Research, vol. 146, no. 2, 1986, pp. 233-240.
http://dx.doi.org/10.1016/0008-6215(86)85042-X
---------- VANCOUVER ----------
Sznaidman, M.L., Cirelli, A.F., de Lederkremer, R.M. Synthesis of 5-O-methyl-d-galactofuranose. Carbohydr. Res. 1986;146(2):233-240.
http://dx.doi.org/10.1016/0008-6215(86)85042-X