Industrial Biotransformations

Oxidase
Rhodococcus erythropolis
● Another chemical route starts from l-ascorbic acid:
HO
OH
3) Flow scheme
Not published.
4) Process parameters
conversion: 50 %
ee: > 98 % for (R)-1, > 90 % for (R)-2
reactor type: fed batch
company: International BioSynthetics, Inc., The Netherlands
5) Product application
● (R)-Isopropylideneglycerol is a useful C 3-synthon in the synthesis of (S)-β-blockers, e.g. (S)metoprolol.
● Also, the (R)-isopropylideneglyceric acid may be used as starting material for the synthesis of
biologically active products.
6) Literature
O
L-1
1 = ascorbic acid
2 = isopropylideneglyceric aldehyde
3 = isopropylideneglycerol
O
HO OH
Fig. 1.X.X.X – 3
Me2CO
● Crosby, J. (1991) Synthesis of optically active compounds: a large scale perspective, Tetrahedron
47, 4789–4846
● Bertola, M. A., Koger, H. S., Phillips, G. T., Marx, A. F., Claassen, V. P. (1987) A process for the
preparation of (R)- and (S)–2,2-R1,R2–1,3-dioxolane-4-methanol, Gist-Brocades NV and Shell
Int. Research, EP 0244912
● Baer, E., Fischer, H. (1948) J. Am. Chem. Soc. 70, 609
O
O
O
O
HO OH
1) NaBH4
2) NaOH
3) H +
4) Pb(OAc)4
EC 1.X.X.X
(R)-3
● Hirth, G., Walther, W. (1985) Synthesis of the (R)- and (S)-glycerol acetonides. Determination
of the optical purity, Helv. Chim. Acta 68, 1863
256
O
O
(R)-2
CHO
NaBH 4
O
O
OH