A new synthesis of 2,5-anhydro-D-mannose derivatives
Keyword(s):
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.
1969 ◽
Vol 47
(17)
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pp. 3271-3273
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2005 ◽
Vol 46
(11)
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pp. 1819-1821
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1952 ◽
Vol 74
(22)
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pp. 5759-5759
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1982 ◽
Vol 47
(9)
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pp. 2415-2422
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1990 ◽
Vol 48
(3)
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pp. 448-449