Divergent Synthesis of All Possible Optically Active Regioisomers of Myo-Inositol Mono- and Bisphosphates

All possible optically active regioisomers of myo-inositol mono- and bisphosphates were synthesized using inositol derivatives suitably protected with various protecting groups (IR n s) as key intermediates. A series of procedures including Novozym 435 catalyzed enzymatic resolution of (3aR,4S,7S,7a...

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Bibliographic Details
Published in:Journal of carbohydrate chemistry 2007-09, Vol.26 (5-6), p.305-327
Main Authors: Seo, Kyung-Chang, Yu, Seok-Ho, Chung, Sung-Kee
Format: Article
Language:English
Subjects:
divergent synthesis
Inositol phosphates
Myo-inositol
Phosphorylation
Protecting groups
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Summary:All possible optically active regioisomers of myo-inositol mono- and bisphosphates were synthesized using inositol derivatives suitably protected with various protecting groups (IR n s) as key intermediates. A series of procedures including Novozym 435 catalyzed enzymatic resolution of (3aR,4S,7S,7aR)-rel-3a,4,7,7a-tetrahydro-2,2-dimethyl-1,3-benzodioxole-4,7-diol diacetate, several protection and deprotection reactions, and acyl migration afforded two enantiomeric pairs of IR 5 and six enantiomeric pairs of IR 4 . Phosphorylation of these key intermediates by the phosphitylation and oxidation procedure gave the target products after removal of the protecting groups.
ISSN:0732-8303
1532-2327
DOI:10.1080/07328300701540225