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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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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Abstract 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.
AbstractList All possible optically active regioisomers of myo-inositol mono- and bisphosphates were synthesized using inositol derivatives suitably protected with various protecting groups (IRns) 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-benzodio xole-4,7- diol diacetate, several protection and deprotection reactions, and acyl migration afforded two enantiomeric pairs of IR5 and six enantiomeric pairs of IR4. Phosphorylation of these key intermediates by the phosphitylation and oxidation procedure gave the target products after removal of the protecting groups.
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.
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 IR5 and six enantiomeric pairs of IR4. Phosphorylation of these key intermediates by the phosphitylation and oxidation procedure gave the target products after removal of the protecting groups. [GRAPHICS]
Author Seo, Kyung-Chang
Yu, Seok-Ho
Chung, Sung-Kee
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crossref_primary_10_1021_acs_orglett_6b01374
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Issue 5-6
Keywords protecting groups
TETRAKISPHOSPHATES
PENTAKISPHOSPHATE
Myo-inositol
inositol phosphates
LITHIUM
phosphorylation
DERIVATIVES
ASSOCIATION
divergent synthesis
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PublicationTitle Journal of carbohydrate chemistry
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Taylor & Francis
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Snippet All possible optically active regioisomers of myo-inositol mono- and bisphosphates were synthesized using inositol derivatives suitably protected with various...
All possible optically active regioisomers of myo- inositol mono- and bisphosphates were synthesized using inositol derivatives suitably protected with various...
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SubjectTerms Biochemistry & Molecular Biology
Chemistry
Chemistry, Organic
divergent synthesis
Inositol phosphates
Life Sciences & Biomedicine
Myo-inositol
Phosphorylation
Physical Sciences
Protecting groups
Science & Technology
Title Divergent Synthesis of All Possible Optically Active Regioisomers of Myo-Inositol Mono- and Bisphosphates
URI https://www.tandfonline.com/doi/abs/10.1080/07328300701540225
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Volume 26
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