FROM CHLOROBENZENE TO A CARBOHYDRATE IN 2 STEPS - A NEW CHEMOENZYMATIC SYNTHESIS OF 2,3-O-ISOPROPYLIDENE-D-ERYTHRURONOLACTONE

Authors
MANDEL M HUDLICKY T KWART LD WHITED GM
Citation
M. Mandel et al., FROM CHLOROBENZENE TO A CARBOHYDRATE IN 2 STEPS - A NEW CHEMOENZYMATIC SYNTHESIS OF 2,3-O-ISOPROPYLIDENE-D-ERYTHRURONOLACTONE, Collection of Czechoslovak Chemical Communications, 58(10), 1993, pp. 2517-2522
Citations number
16
Categorie Soggetti
Chemistry
Journal title
Collection of Czechoslovak Chemical Communications → ACNP
ISSN journal
00100765
Volume
58
Issue
10
Year of publication
1993
Pages
2517 - 2522
Database
ISI
SICI code
0010-0765(1993)58:10<2517:FCTACI>2.0.ZU;2-O
Abstract
Controlled oxidation of chloroepoxide V with two equivalents of sodium periodate furnished 2,3-O-isopropylidene-D-erythruronolactone (I) in 63% yield. This procedure was augmented by combining the protection of diol III, the oxidation of acetonide IV to V, and the subsequent oxid ative cleavage to I into one operation which yielded, on medium scale, the title lactone in 51% yield. Detailed procedure of preparation and physical constants are provided for lactone I.