2.

The Fischer-to-Haworth Shortcut: For C2,

C3, and C4, Right =Down and Left =Up.
Having walked through the process the long way, let’s try to come up with a shortcut for
this process.

Compare the Fischer projection of D-glucose to the final Haworth:

• C2–OH is on the right side of the Fischer and ends up on the bottom of the
Haworth.
• C3–OH is on the left side of the Fischer and ends up on the top of the Haworth
• C4–OH is on the right side of the Fischer and ends up on the bottom of the
Haworth
This gives us the following shortcut. If a group is on the left side of the Fischer, it will end
up on the top face of the Haworth, and if it is on the right side of the Fischer, it will end up
on the bottom face of the Haworth.

Right-down, left-up. (for C-2, C-3, and C-4, at least)

What about C5 and C1 ?

3. What About C5 and C1 ?

In our example the C5-OH was on the right side of the Fischer, which made it (by definition)
a D-sugar. We saw that C6 (the CH2OH) ended up on the top of the Haworth, so we can make
a generalization:

• for D-sugars, the C6 carbon will end up on the top of the Haworth
• for L-sugars, the C6 carbon will end up on the bottom of the Haworth.
That leaves us with C1. The hydroxyl group on C1 can end up in one of two configurations –
either “up” on our Haworth, or “down”- depending on which face of the carbonyl is
attacked.

The standard terminology for these two configurations at the C-1 carbon (sometimes called
the “anomeric carbon“) uses the terms alpha (α) and beta (β).

In the “α” configuration, the C1-OH is on the opposite face of the ring as the C5 substituent
[CH2OH in this case]. For a D-sugar, therefore, the C1-OH points down.
In the β configuration, the C1-OH is on the same face as the C5 substituent. (i.e. for a D-
sugar, the C1-OH points up, as does the CH2OH attached to C5 ).