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Type: Artigo de periódico
Title: Synthesis Of Benzyl And Methyl 3-benzamido-2,3,6-trideoxy-2-fluoro-β-l-galactopyranoside: Protected C-2 Fluoro Analogues Of Daunosamine
Author: Brito Baptistella L.H.
Marsaioli A.J.
de Souza Filho J.D.
de Oliveira G.G.
de Oliveira A.B.
Dessinges A.
Castillon S.
Olesker A.
That Thang T.
Lukacs G.
Abstract: The reaction of benzyl 2-benzamido-4,6-O-benzylidene-2-deoxy-3-O-tosyl-α-d-glucopyranoside or benzyl 4,6-O-benzylidene-2,3-benzoylepimino-2,3-dideoxy-α-d-allopyranoside with anhydrous tetrabutylammonium fluoride in hexamethylphosphoric triamide gave ∼40% of benzyl 3-benzamido-4,6-O-benzylidene-2,3-dideoxy-2-fluoro-α-d-altropyranoside (6a). Transformation of 6a into benzyl 3-benzamido-2,3,6-trideoxy-2-fluoro-α-d-arabino-hex-5-enopyranoside (13a) was carried out by well-established methodology. Hydrogenation of the double bond in 13a furnished the title compound in good yield. Methyl 3-benzamido-2,3,6-trideoxy-2-fluoro-β-l-galactopyranoside was also prepared in nine steps from 2-amino-2-deoxy-d-glucose. © 1985.
Citation: Carbohydrate Research. , v. 140, n. 1, p. 51 - 59, 1985.
Rights: fechado
Identifier DOI: 10.1016/0008-6215(85)85048-5
Date Issue: 1985
Appears in Collections:Unicamp - Artigos e Outros Documentos

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