SOME OPEN-CHAIN DERIVATIVES OF GLUCOSE AND MANNOSE
The dimethyl thioacetals of D-glucose and D-mannose have been condensed with acetone. Mannose dimethyl thioacetal forms a crystalline 3,4:5,6-di-O-isopropylidene derivative while glucose forms a mixture of the crystalline 3,4:5,6-di-O-isopropylidene and syrupy 2,3:5,6-di-O-isopropylidene isomers. These three di-O-isopropylidene dimethyl thioacetals have been converted via crystalline intermediates into the corresponding di-O-isopropylidene dimethyl acetals. These derivatives are suitable open-chain compounds for use in Koenigs–Knorr syntheses and provide (a) mannose with the C2 hydroxyl free, (b) glucose with the C2 hydroxyl free, and (c) glucose with the C4 hydroxyl free.
1959 ◽
Vol 81
(7)
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pp. 1729-1734
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1980 ◽
pp. 372-377
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1965 ◽
Vol 87
(8)
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pp. 1757-1764
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1913 ◽
Vol 103
(0)
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pp. 1689-1704
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1967 ◽
Vol 8
(32)
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pp. 3067-3070
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