Fluoro-myo-inositol

VlL-l-Deoxy-l-fluoro-myo-inositol (393) and (+)-lD-l-deoxy-l-fluoro-m> oinositol (394) have been prepared from myo-inositol through multi-step reactions involving DAST treatment. [Pg.152]

OH - F.1 Reaction of neat DAST with the optically active natural inositol quebrachitol (1) results in two products, each formed by replacement of one of the two axial hydroxyl groups of 1. However, on deprotection (BBr3) each provides (— )-fluoro-myo-inositol (4). [Pg.128]

Figure 2. Target Deoxyfluorocyclitols 1 -Deo3cy-1 -fluoro-scyllo-inositol (2) 4(6)-Deoxy-4(6)-fluoro-myo-inositol (3) 5-Deoxy-5-fluoro-myo-inositol (4) 2-Deoxy-2-fluoro-neo-inositol (5) 5-Deoxy-5,5-dif luoro-myo-inosi to 1 (6).

Deoxy-5-fluoro-myo-inositol (4) and 2-deoxy-2-fluoro-neo-inositol... [Pg.47]

Figure 4. Synthesis of 5-deoiy-5-fluoro-myo-inositol (4) and 2-deoxy-2-fluoro-neo-inositol (5). Reagents a. Diethylaminosulfur trifluoride (dAST) b. H2 - Pd(0H)2/C, HO Ac c. AC2O - pyridine.

The ability of PI synthetase to use 5-deoxy-5-fluoro-myo-inositol (4) as a substrate was confirmed by use of a radiolabeled compounds as shown in Figure 7. PI synthetase incorporated the analog into lipid in a time-dependent manner. The incorporation was absolutely dependent on the presence of CDP-diglyceride and was inhibited by the presence of myo-inositol (1) in the incubation mixture, as expected for PI synthetase. Chromatography of the reaction mixture revealed that a single radiolabeled product was formed with a mobility similar to, but distinct from, that of PI. Subsequent analysis has shown that the product is converted to a water-soluble form on mild alkaline hydrolysis and yields 5-deoxy-5-fluoro-myo-inositol (4) on treatment with phospholipase D, in agreement with the formation of phosphatidyl-5-deoxy-5-fluoro-myo-inositol as the product (data not shown). Determination of the absolute structure of these phospholipids awaits large-scale enzymatic synthesis, isolation of the product, and studies by mass spectrometry and NMR spectroscopy. [Pg.54]

Figure 7. Incorporation of [ H]5-deoxy-5-fluoro-myo-ino8itol into lipid by PI synthetase of rat brain. [5H]5-deoiy-5-fluoro-myo-inositol (25 pM, 4 yCi/mL) was incubated with 5 CDP-diglyceride and solubilized rat brain microsomes at 37 °C as described in ref. 34. At the indicated times, 40-pL aliquots were removed, the reaction was terminated by the addition of trichloroacetic acid, and the lipid-soluble radioactivity was determined (o). Incubations without CDP-diglyceride (A) or in the presence of 5 JuM myo-inositol ( ) were also performed. The values shown are the mean SEM for three independent incubations. This result is representative of three separate experiments.

Figure 8. Incorporation of 5-

$Figure 8. Incorporation of 5-<Ieoxy-5-fluoro-myo-inositol (4) into intracellular pools and lipids of L1210 murine leukemia cells in culture. Exponentially growing LI 210 cells were concentrated by centrifugation to 2 x lo" cells/mL in inositol-free Fisher s medium and incubated at 37 °C with 4 yCi/mL [ H]myo-inositol (upper panel) or H]5-<ieoxy-5-fluoro-myo-inositol (lower panel). The specific activity was 0.17 Ci/mmol for both compounds, and the concentrations were 25 ViM. At the indicated times, samples of the cell suspension were removed, and the cells were collected by centrifugation through a layer of silicone oil and fractionated into lipid-soluble and water-soluble fractions. The values shown are the mean of duplicate incubations, and the result is representative of three independent experiments.$

The preparations of 5-deoxy-5-fluoro-myo-inositol, iL-l-deoxy-l-fluoro-myo-inositol, 1d-4-deoxy-4-fluoro-myo-inositol, lL-4-deoxy-4-fluoro-/nyo-inositol, and 2-deoxy-2-fluoro-ffiyo-inositol by conventional chemistry from known racemic /nyo-inositol derivatives and resolution by use of (SH-)-camphamic acid have been described. In a similar way the nthesis of 1-deoxy-l-fluoro-scyWo-inositol, 2-deoxy-2,2-difluoro-my< -inositol, D,L-2-deoxy-2-fluoro-scy/Zo-inositol 1,4,5-triphosphate and D -2-deoxy-2,2-difluoro-ffi) o-inositol 1,4,5-triphosphate have been described. The synthesis of silyl protected myo-inositols with free hydroxyls at 1-, 5-, 6-, 1,4-, 4,5-, 5,6-, 1,4,5-, and 1,4,6-positions has been described. ... [Pg.200]

L-1-Deoxy-1-fluoro-myo-inositol (51) has been prepared from myo-inositol by the procedure outlined in Scheme 14, including a camphonate resolution. [Pg.187]

Acetalated myo-inositol derivatives have been converted by standard reactions into intermediates required for the total synthesis of sugarotoxin and some of its analogues, which are 6-0-acyl derivatives of myo-inositol.Quebrachitol reacts with DAST to a deoxy-fluoro derivative which, on demethylation, gave the fluoro-inositol (54), a cellular replication inhibitor.Deoxy-fluoro-myo-inositols have been prepared, and their behaviour as substrates for phosphatidyl-inositol synthetase has been reported. 2-C-fluoromethyl-myo-inositol (55) has been prepared conventionally from an exocyclic oxiran precursor. [Pg.186]

The preparation of 2-deoxy-2-fluoro-myo-inositol and l-deoxy-l-fluoro-scy//o-inositol together with 2-deoxy-2-fluoro-myo-[2- H]inositol and l-deoxy-l-fluoro-scy//o-... [Pg.209]

Racemic 4-deoxy-4-fluoro-myo-inositol has been made by reaction of 66 with DAST (retention of configuration observed) then hydrogenolysis, and 2-deoxy-2-fluoro-myo-inositol, 2-deoxy-2-fluoro-scy//o-inositol and 2-deoxy-2,2-difluoro-myo-inositol have been synthesized from 3,4,5,6-tetra-O-benzyl-myo-inositol via a selective benzoylation at the equatorial hydroxyl group and subsequent standard chemistry. ... [Pg.239]

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