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Dolbier HW Solutions 617

Dolbier HW Solutions 617 - 711 CARBOHYDRATES The pyranose...

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The pyranose form arises by closure to a six-membered cyclic hemiacetal, with the C-5 hydroxyl group undergoing nucleophilic addition to the carbonyl. In the b -pyranose form of D -xylose the anomeric hydroxyl group is up. The preferred conformation of b - D -xylopyranose is a chair with all the hydroxyl groups equatorial. ( d ) L -Xylose is the mirror image of D -xylose. To construct the furanose form of L -xylose, the hydroxyl at C-4 needs to be brought into the proper orientation to form a f ve-membered ring. The a anomeric hydroxyl group is up in the L series. ( e ) Methyl a - L -xylofuranoside is the methyl glycoside corresponding to the structure just drawn. (
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