Phosphatidyl inositol isopropylidene derivatives: synthesis, characterizaton and use as synthetic intermediates
β Scribed by Naoki Noda; Roy W. Keenan
- Book ID
- 103040926
- Publisher
- Elsevier Science
- Year
- 1990
- Tongue
- English
- Weight
- 783 KB
- Volume
- 53
- Category
- Article
- ISSN
- 0009-3084
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β¦ Synopsis
To provide starting material for the synthesis of phosphatidyl inositol phosphates and inositol phosphates, isopropylidenes of phosphatidyl inositols were prepared. Phosphatidyl inositol obtained from yeast was converted into a mono-and two di-O-isopropylidenes fractions by transacetalation with 2,2-dimethoxypropane. Three isopropylidenes fractions were isolated and characterized by mass spectral analysis and comparison of the hydrolysis products of these fractions to know isopropylidenes of myo-inositol. The isopropylidenes were phosphatidtyl-2,3-O-isopropylidene-inositois, phosphatidyl-2,3:4,5-di-O-isopropylideneinositols and phosphatidyl-2,3:5,6-di-O-isopropylidene-inositols. These compounds are intermediates for the stereospecifie synthesis of different phosphatidyl inositol phosphates, inositol phosphates and analogs of these compounds. Using the di-O-isopropylidenes as starting materials, both phosphatidyl inositol-4-phosphate and phosphatidyl inositoi-6-phosphates were synthesized. Neither compound had been prepared synthetically before and phosphatidyl inositol-6-phosphate is not naturally occurring.
π SIMILAR VOLUMES
4, ## Experimental Part 1. General. Solvents were either reagent or technical grade and when necessary were purified and dried by distillation from an appropriate dessiccant under N,. S o h . after reactions and extractions were evaporated at ca. 20 Torr. HMPA = hexamethylphosphoric triamide. M.p