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 inJournal of carbohydrate chemistry Vol. 26; no. 5-6; pp. 305 - 327
Main Authors Seo, Kyung-Chang, Yu, Seok-Ho, Chung, Sung-Kee
Format Journal Article
LanguageEnglish
Published PHILADELPHIA Taylor & Francis Group 01.09.2007
Taylor & Francis
Subjects
Biochemistry & Molecular Biology
Chemistry
Chemistry, Organic
divergent synthesis
Inositol phosphates
Life Sciences & Biomedicine
Myo-inositol
Phosphorylation
Physical Sciences
Protecting groups
Science & Technology
protecting groups
TETRAKISPHOSPHATES
PENTAKISPHOSPHATE
Myo-inositol
inositol phosphates
LITHIUM
phosphorylation
DERIVATIVES
ASSOCIATION
divergent synthesis
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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.
Bibliography:ObjectType-Article-2
SourceType-Scholarly Journals-1
ObjectType-Feature-1
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ISSN:0732-8303
1532-2327
DOI:10.1080/07328300701540225