Treatment of B-D-glucose with methanol in the presence of an acid catalyst converts it into a mixture of two compounds called methyl glucosides (Section 25.3A). CH,OH * CH,OH CH,OH H H OH + CH,OH H H 5. H H OCH, H H* 4 4 ОН H -H,O OH H ОН H ÓCH, НО НО НО 2 ОН H ОН H ОН B-D-Glucose Methyl B-D-glucoside Methyl a-D-glucoside In these representations, the six-membered rings are drawn as planar hexagons.
Treatment of B-D-glucose with methanol in the presence of an acid catalyst converts it into a mixture of two compounds called methyl glucosides (Section 25.3A). CH,OH * CH,OH CH,OH H H OH + CH,OH H H 5. H H OCH, H H* 4 4 ОН H -H,O OH H ОН H ÓCH, НО НО НО 2 ОН H ОН H ОН B-D-Glucose Methyl B-D-glucoside Methyl a-D-glucoside In these representations, the six-membered rings are drawn as planar hexagons.
Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter16: Aldehydes And Ketones
Section: Chapter Questions
Problem 16.67P: Treatment of -D-glucose with methanol in the presence of an acid catalyst converts it into a mixture...
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Propose a mechanism for this conversion and account for the fact that only the -OH on carbon 1 is transformed into an -OCH3 group.
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