A Synthesis of 1 D ‐ and 1 L ‐ myo ‐Inositol 1,3,4,5,‐Tetraphosphate

A synthesis of 1 D ‐ and 1 L ‐ myo ‐inositol 1,3,4,5,‐tetraphosphate ( 1a and 1b resp.) is described. The dibenzylated myo ‐inositola 9a and 9b , which, by phosphorylation, gave 1a and 1b , respectively, were prepared via two routes. On the one hand, the racemate 3a/3b , obtained from myo ‐inositol,...

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Veröffentlicht in:Helvetica chimica acta 1988-08, Vol.71 (5), p.1367-1378
Hauptverfasser: Baudin, Gisèle, Glänzer, Brigitte I., Swaminathan, Kivalur S., Vasella, Andrea
Format: Artikel
Sprache:eng
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Zusammenfassung:A synthesis of 1 D ‐ and 1 L ‐ myo ‐inositol 1,3,4,5,‐tetraphosphate ( 1a and 1b resp.) is described. The dibenzylated myo ‐inositola 9a and 9b , which, by phosphorylation, gave 1a and 1b , respectively, were prepared via two routes. On the one hand, the racemate 3a/3b , obtained from myo ‐inositol, was resolved by its transformation into the diastereoisomeric carbamates 5a and 5b . Benzylation and deprotecton of 5a and 5b gave the enantiomers 9a and 9b , respectively. On the other hand, treatment of the diester 18 with pig liver esterase gave the ester 21a with high enantiomeric excess. Benzylation and deprotection of 21a yielded 9b . The dibenzyl derivative 9a was obtained using the same enzymatic hydrolysis followed by a protection‐deprotection sequence.
ISSN:0018-019X
1522-2675
DOI:10.1002/hlca.19880710548