Convenient synthesis of 4,6-di-O-benzyl-myo-inositol and myo-inositol 1,3,5-orthoesters
Metadata of CSIR Papers
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| Title |
Convenient synthesis of 4,6-di-O-benzyl-myo-inositol and myo-inositol 1,3,5-orthoesters
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| Creator |
Praveen, T
Shashidhar, MS |
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| Subject |
Biochemistry & Molecular Biology; Chemistry, Applied; Chemistry, Organic
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| Description |
Convenient high yielding methods for the preparation of 4,6-di-O-benzyl-myo-inositol, myo-inositol 1,3,5-ortho-formate and myo-inositol 1,3,5-orthoacetate, without involving chromatography are described. Myo-inositol was converted to racemic 2,4-di-O-benzoyl-myo-inositol 1,3,5-orthoformate by successive treatment with triethyl ortho-formate and benzoyl chloride. The dibenzoate obtained on benzylation with benzyl bromide and silver(I) oxide gave 2-O-benzoyl-4,6-di-O-benzyl-myo-inositol 1,3,5-orthoformate. Deprotection of the benzoate and the orthoformate with isobutylamine and aqueous trifluoroacetic acid, respectively gave 4,6-di-O-benzyl-myo-inositol in an overall yield of 67%. Myo-inositol orthoformate and orthoacetate were prepared and isolated as their tribenzoates. The free orthoesters were regenerated by deprotection of the benzoates by aminolysis with isobutylamine. (C) 2001 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 |
2011-09-24T09:14:42Z
2011-09-24T09:14:42Z 2001 |
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| Type |
Article
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| Identifier |
CARBOHYDRATE RESEARCH
0008-6215 http://hdl.handle.net/123456789/24133 |
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| Language |
English
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