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 |
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Hauptverfasser: | , , , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
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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. |
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ISSN: | 0018-019X 1522-2675 |
DOI: | 10.1002/hlca.19880710548 |