Sulfonate protecting groups. Regioselective sulfonylation of myo-inositol orthoesters - improved synthesis of precursors of D- and L-myo-inositol 1,3,4,5-tetrakisphosphate, myo-inositol 1,3,4,5,6-pentakisphosphate and related derivatives
Metadata of CSIR Papers
View Archive Info| Field | Value | |
| Title |
Sulfonate protecting groups. Regioselective sulfonylation of myo-inositol orthoesters - improved synthesis of precursors of D- and L-myo-inositol 1,3,4,5-tetrakisphosphate, myo-inositol 1,3,4,5,6-pentakisphosphate and related derivatives
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| Creator |
Sureshan, KM
Shashidhar, MS Praveen, T Gonnade, RG Bhadbhade, MM |
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| Subject |
Biochemistry & Molecular Biology; Chemistry, Applied; Chemistry, Organic
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| Description |
The regioselectivity of sulfonylation of myo-inositol orthoesters was controlled by the use of different bases to obtain the desired sulfonate. Monosulfonylation of myo-inositol orthoesters in the presence of one equivalent of sodium hydride or triethylamine resulted in the sulfonylation of the 4-hydroxyl group. The use of pyridine as a base for the same reaction resulted in sulfonylation of the 2-hydroxyl group. Disulfonylation of these orthoesters in the presence of excess sodium hydride yielded the 4,6-di-O-sulfonylated orthoesters. However, the use of triethylamine or pyridine instead of sodium hydride yielded the 2,4-di-O-sulfonylated orthoester. Sulfonylated derivatives of myo-mositol orthoesters were stable to conditions of O-alkylation but were cleaved using magnesium/methanol or sodium methoxide in methanol to regenerate the corresponding myo-inositol orthoester derivative. These new methods of protection-deprotection have been used: (i) for the efficient synthesis of enantiomers of 2,4-di-O-benzyl-myo-inositol, which are precursors for the synthesis Of D- and L-myo-inositol 1,3,4,5-tetrakisphosphate; (ii) for the preparation of 2-0-benzyl-myo-inositol which is a precursor for the preparation of myo-inositol 1,3,4,5,6-pentakisphosphate. (C) 2002 Elsevier Science Ltd. All rights reserved.
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| Publisher |
ELSEVIER SCI LTDOXFORDTHE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, OXON, ENGLAND
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| Date |
2011-09-24T09:49:45Z
2011-09-24T09:49:45Z 2002 |
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| Type |
Article
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| Identifier |
CARBOHYDRATE RESEARCH
0008-6215 http://hdl.handle.net/123456789/24203 |
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| Language |
English
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