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

Baudin Gisèle | Zendy; Glänzer Brigitte I. | Zendy; Swaminathan Kivalur S. | Zendy; Vasella Andrea | Zendy

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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.

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