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A simple and practical resolution of 1,2:4,5-di-O-isopropylidene-myo-inositol

✍ Scribed by Kana M. Sureshan; Toru Yamasaki; Minoru Hayashi; Yutaka Watanabe

Publisher
Elsevier Science
Year
2003
Tongue
English
Weight
152 KB
Volume
14
Category
Article
ISSN
0957-4166

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✦ Synopsis

An efficient method for the resolution of 1,2:4,5-di-O-isopropylidene-myo-inositol has been developed. The diketal was converted to diastereomeric 3,6-di-O-mandelates by the reaction with (S)-O-acetylmandeloyl chloride. Both the diastereomers could be separated by sequential crystallization in multi-gram quantities. The enantiomers of the diol were obtained by removal of the chiral auxiliaries. Also the trans-isopropylidene was cleaved efficiently to obtain another pair of chiral diols.

πŸ“œ SIMILAR VOLUMES

Crystal structures of (Β±)-1,2:4,5-di-O-i
Crystal structures of (Β±)-1,2:4,5-di-O-isopropylidene-myoinositol and (Β±)-1,2:5,6-di-O-isopropylidene-myo-inositol: a conformational analysis
✍ Sung-Kee Chung; Youngha Ryu; Young-Tae Chang; Dongmok Whang; Kimoon Kim πŸ“‚ Article πŸ“… 1994 πŸ› Elsevier Science 🌐 English βš– 325 KB

f )-1,2:4,5-Di-0-isopropylidene-myo-inositol (11, C,2H,0,, crystallises in the mopoclinic space group, C2/c with unit-cell dimensions a = 22.587(3), b = 5.4204(3), and c = 22.174(4) A. (\*)\_1,2:5,6di-0-isopropylidene-myo-inositol (2), C,,H,O,, cOmtallises in the monoclinic space group, P2, /n with

The synthesis and resolution of (Β±)-1,4-
The synthesis and resolution of (Β±)-1,4-diO-benzyl-2,3-O-isopropylidene-myo-inositol
✍ Trupti Desai; Jill Gigg; Roy Gigg; EloΓ­sa MartΓ­n-Zamora; Nathalie Schnetz πŸ“‚ Article πŸ“… 1994 πŸ› Elsevier Science 🌐 English βš– 700 KB

An improved procedure for the preparation of 1,2-O-isopropylidene-nqVo-inositol is described. Racemic 1,4-di-O-benzyl-2,3-O-isopropylidene-myo-inositol was prepared by tinmediated benzylation of 1,2-0-isopropylidene-myo-inositol and resolved readily by crystalk sation of the o-camphanates. The use o