Drawing Haworth Formula

D-Glucose exists primarily as a cyclic hemiacetal

1

CHO
2
H
OH
3
HO
H
4
H
OH
5
H
OH
6
CH2OH
Linear Form of D-glucose
Fischer Projection

H
H
4

OH

OH
OH
3

H
2

CH2OH
OH
H
4
H
OH
H 1
CHO
2
OH 3
5

CH2OH
1

CHO

H
OH
Redrawing glucose helps
to see ring stereochemistry.

OH

HO

O OH
1
2

HO
-D-glucopyranose

HO
4

HO

6
5

O
2

OH

1
2

OH

OH

-L-arabinofuranose

OH

OH

Haworth formula

1
2

OH
HO
-D-glucopyranose

HO

=
HO
HO 4
HO

CHO
Example - L-arabinose to
2
-furanose form
H
OH
3
2 = R = down
HO
H
3 = S = up
4
4 = S = L = CH2OH down HO 5 H
CH2OH

HO

HO
4

OH

HO
HO 4
HO

Rules for converting a Fischer projection to a Haworth

formula.
1) Draw proper sized ring: pyranose = 6-membered
furanose = 5-membered.
2) C-1 of the sugar (anomeric carbon) is always right
corner of the ring. Number carbons clockwise around
the ring.
3) D-sugar = CH2OH up; L-sugar = CH2OH down
4) has OH opposite to CH2OH; has OH same side
as CH2OH
5) Other stereocenters: -OH right (R) = down; -OH left
(S) = up

Formation of the
hemiacetal gives a new
stereocenter, the
anomeric carbon (C-1).

5
3

O
2

HO

OH Cyclic form
chair conformation