7. What About Five-Membered Rings?

(Furanoses)
Haworth projections can be used for five-membered ring sugars (i.e. furanoses) too.

So how do we convert a Fischer to a five-membered Haworth?

The shortcut is essentially the same, but since the C4-OH is usually forming the ring instead
of C5-OH, the mnemonic right → down and left → up only applies for the two carbons
adjacent to the carbonyl (usually C2 and C3).

So if the C4-OH is forming the ring, and if it’s on the right in the Fischer (i.e. D, for a
pentose), then the C5 will point up on the Haworth.

Alpha and beta in a furanose are assigned by comparing the orientation of the C1-OH with
the C4 substituent (not the C5 substituent, as with a pyranose).

Here’s D-ribose converted into its α-furanose Haworth projection. [Notice that the C1-OH is
on the opposite face of the molecule from the C4– substituent (CH2OH), which makes the
configuration alpha (α) ]

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