A new 6-C-alkylation from an alkyl mannofuranoside 5, 6-cyclic sulfate
T Gourlain, A Wadouachi, D Beaupère
Index: Gourlain, Thierry; Wadouachi, Anne; Beaupere, Daniel Carbohydrate Research, 2000 , vol. 324, # 1 p. 66 - 73
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Citation Number: 7
Abstract
Methyl 6-C-alkyl-6-deoxy-α-d-mannofuranoside derivatives have been synthesized from methyl 2, 3-O-isopropylidene-5, 6-O-sulfuryl-α-d-mannofuranoside (1). In a Path A, reaction of the 5, 6-cyclic sulfate 1 with 2-lithio-1, 3-dithiane afforded 2-(methyl 6-deoxy-2, 3-O- isopropylidene-α-d-mannofuranosid-6-yl)-1, 3-dithiane (2). Treatment of 2 with n-butyllithium then alkyl iodide gave the corresponding 2-(methyl 5-O-alkyl-6-deoxy-2, 3-O- ...
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