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.

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Chapter21: Biochemistry
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Which of the two products has the chair conformation of greater stability? Explain.

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.
Transcribed Image Text: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.
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