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A Synthesis of 1 D ‐ and 1 L ‐ myo ‐Inositol 1,3,4,5,‐Tetraphosphate
Author(s) -
Baudin Gisèle,
Glänzer Brigitte I.,
Swaminathan Kivalur S.,
Vasella Andrea
Publication year - 1988
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19880710548
Subject(s) - chemistry , enantiomer , inositol , hydrolysis , esterase , derivative (finance) , pig liver , stereochemistry , transformation (genetics) , enzyme , organic chemistry , biochemistry , receptor , financial economics , economics , gene
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.