Chemoenzymatic synthesis of the epimeric 6C-methyl-D-mannoses from toluene

Citation
Mg. Banwell et al., Chemoenzymatic synthesis of the epimeric 6C-methyl-D-mannoses from toluene, NEW J CHEM, 25(1), 2001, pp. 3-7
Citations number
22
Categorie Soggetti
Chemistry
Journal title
NEW JOURNAL OF CHEMISTRY
ISSN journal
11440546 → ACNP
Volume
25
Issue
1
Year of publication
2001
Pages
3 - 7
Database
ISI
SICI code
1144-0546(2001)25:1<3:CSOTE6>2.0.ZU;2-M
Abstract
The title compounds 1 and 2, which are effective and specific inhibitors of phosphohexomutases, have been prepared in enantiomerically pure form from toluene. The initial step of the reaction sequence involves enzymatic cis-1 ,2-dihydroxylation of toluene by E. coli JM109 (pDTG601) to give the cis-1, 2-dihydrocatechol 3. The latter compound is then converted, via a series of chemical oxidation and reduction steps, into compounds 1 and 2. The X-ray crystal structures of the bis-acetonide derivatives 11, 13 and 14 have been determined.