A new synthesis of 2,5-anhydro-D-mannose derivatives | Zendy

Juan Antonio López Sastre | Zendy; José Molina Molina | Zendy; Dolores Portal Olea | Zendy; Cristina Romero-Avila | Zendy

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A new synthesis of 2,5-anhydro-D-mannose derivatives

Author(s) -

Juan Antonio López Sastre,

José Molina Molina,

Dolores Portal Olea,

Cristina Romero-Avila

Publication year - 1988

Publication title -

canadian journal of chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.323

H-Index - 68

eISSN - 1480-3291

pISSN - 0008-4042

DOI - 10.1139/v88-462

Subject(s) - chemistry , sodium methoxide , mannose , derivative (finance) , methanol , acetal , monoxide , acetylation , organic chemistry , medicinal chemistry , biochemistry , financial economics , economics , gene

Penta-O-acetyl-D-glucose diethyl dithioacetal monoxide 3 was obtained by oxidation of penta-O-acetyl-D-glucose diethyl dithioacetal 2 with 3-chloroperbenzoic acid. By reaction of 3 with sodium methoxide in methanol and further acetylation, 3,4,6-tri-O-acetyl-2,5-anhydro-D-mannose-diethyl dithioacetal monoxide 8 and the reduction product 3,4,6-tri-O-acetyl-2,5-anhydro-1,1-bis(ethylthio)-1-deoxy-D-arabino-hex-1-enitol 4 were obtained. Reduction of 8 yielded the corresponding dithioacetal derivative 9, which was converted to 3,4,6-tri-O-acetyl-2,5-anhydro-D-mannose diethyl acetal 11.

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