STRUCTURE OF (+ -)-1,2-4,5-DI-O-CYCLOHEXYLIDENE MYOINOSITOL AND SYNTHESIS OF MYOINOSITOL 3-PHOSPHATE VIA ITS PHOSPHORYLATION WITH 4-DIMETHYL-5-PHENYL-1,3,2-OXAZAPHOSPHOLIDIN-2-ONE/

Authors
SPIERS ID SCHWALBE CH BLAKE AJ SOLOMONS KRH FREEMAN S
Citation
Id. Spiers et al., STRUCTURE OF (+ -)-1,2-4,5-DI-O-CYCLOHEXYLIDENE MYOINOSITOL AND SYNTHESIS OF MYOINOSITOL 3-PHOSPHATE VIA ITS PHOSPHORYLATION WITH 4-DIMETHYL-5-PHENYL-1,3,2-OXAZAPHOSPHOLIDIN-2-ONE/, Carbohydrate research, 302(1-2), 1997, pp. 43-51
Citations number
35
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Carbohydrate research → ACNP
ISSN journal
00086215
Volume
302
Issue
1-2
Year of publication
1997
Pages
43 - 51
Database
ISI
SICI code
0008-6215(1997)302:1-2<43:SO(-MA>2.0.ZU;2-O
Abstract
The crystal structure of (+/-)-1,2;4,5-di-O-cyclohexylidene myo-inosit ol, refined to R=2.9%, shows interestingly disordered (flip-flop) hydr ogen bonding. The higher reactivity of the 1/3 positions (rather than 4/6) has been evaluated using semi-empirical calculations. This diol h as been phosphorylated with ,4-dimethyl-5-phenyl-1,3,2-oxazaphospholid in-2-one and the diastereoisomer derived from phosphorylation at the 3 -position was isolated by crystallisation, Deprotection with TFA/H2O t hen H-2/Pd-C afforded myo-inositol 3-phosphate in only four steps from myo-inositol. (C) 1997 Elsevier Science Ltd.