- Sulfonate protecting groups. Synthesis of O- and C-methylated inositols: D- and L-ononitol, D- and L-laminitol, mytilitol and scyllo-inositol methyl ether
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Syntheses of d- and l-ononitol, d- and l-laminitol, mytilitol and scyllo-inositol methyl ether starting from myo-inositol are described. One or two of the myo-inositol 1,3,5-orthoformate hydroxyl groups were protected as tosylates. These mono or ditosylat
- Sarmah, Manash P.,Shashidhar, Mysore S.,Sureshan, Kana M.,Gonnade, Rajesh G.,Bhadbhade, Mohan M.
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p. 4437 - 4446
(2007/10/03)
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- Stereoselective oxidation of protected inositol derivatives catalyzed by inositol dehydrogenase from Bacillus subtilis
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Inositol dehydrogenase (EC 1.1.1.18) from Bacillus subtilis is shown to have a nonpolar cavity adjacent to the active site, allowing racemic protected inositol derivatives such as 4-O-benzyl-myo-inositol to be recognized with very high apparent stereoselectivity.
- Daniellou, Richard,Phenix, Christopher P.,Tam, Pui Hang,Laliberte, Michael C.,Palmer, David R. J.
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p. 401 - 403
(2007/10/03)
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- Racemic 2,4-di-O-benzoyl-myo-inositol 1,3,5-orthoformate: A versatile intermediate for the preparation of myo-inositol phosphates
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The versatility of racemic 2,4-di-O-benzoyl-myo-inositol 1,3,5- orthoformate as an intermediate for the preparation of protected myo- inositol derivatives is demonstrated. Procedures described provide simple access to several protected myo-inositol derivatives which are intermediates for the preparation of myo-inositol phosphates and racemic ononitol.
- Das, Tanya,Shashidhar, Mysore S.
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p. 165 - 168
(2007/10/03)
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- Stereochemical observations on the bromate induced monobromopentahydroxylation of benzene by catalytic photoinduced charge transfer osmylation. A concise synthesis of (±)-pinitol
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The use of lower temperatures in the title reaction favours the formation of the neo diastereoisomer of the deoxybromoinositol whose diisopropylidene derivative can be converted in three steps to (±)-pinitol.
- Jung, Pierre M. J.,Motherwell, William B.,Williams, Alvin S.
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p. 1283 - 1284
(2007/10/03)
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- Total synthesis of (+)- and (-)-ononitol
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A practical, five-step synthetic sequence for conversion of myo-inositol into enantiomerically pure (+)- and (-)-ononitols in 17% and 18% overall yield, respectively, has been developed.
- Pietrusiewicz,Salamonczyk
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p. 1863 - 1867
(2007/10/02)
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- An effective strategy for the synthesis of 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-chiro- and -D-myo-inositol 1-phosphate related to putative insulin mimetics
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Two glycosylinositol phosphates related to putative insulin mimetics, 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-chiro-inositol 1-phosphate (1) and 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol 1-phosphate (2), have been synthesized from selectively protected and enantiomerically pure D-chiro- and myo-inositol derivatives. The D-chiro-inositol unit was prepared in a multigram scale from D-glucose using the Ferrier's carbocyclization route, and it was transformed into the corresponding myo epimer by an oxidation-reduction sequence. The trichloroacetimidate method was applied efficiently for the key glycosylation of the inositol derivatives.
- Jaramillo,Chiara,Martin-Lomas
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p. 3135 - 3141
(2007/10/02)
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- Approaches to the synthesis of glycosyl phosphatidyl inositols. Enantioselective synthesis of optically active chiro- and myo-inositols
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An efficient synthetic strategy to optically active conveniently substituted D-chiro (5) and D-myo-inositol (10) derivatives has been developed starting from methyl α-D-glucopyranoside. Compounds 5 and 10 constitute valuable intermediates for the preparation of glycosyl phosphatidyl inositols.
- Jaramillo,Martin-Lomas
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p. 2501 - 2504
(2007/10/02)
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- Mikrobial Oxidation in Synthesis: Preparation of (+)- and (-)-Pinitol from Benzene
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Microbial oxidation with Pseudomonas putida of benzene affords cis-1,2-dihydroxycyclohexa-3,5-diene (2) which may be converted in five steps and 49percent overall yield to (+/-)-pinitol.Resolution of an intermediate alcohol (6) with menthoxyacetyl chloride provides optically pure materials which may be independently transformed to (+)- or (-)-pinitol.Demethylation conditions for pinitol together with further reactions of (2) and related compounds were investigated.
- Ley, Steven V.,Sternfeld, Francine
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p. 3463 - 3476
(2007/10/02)
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- The Allyl Group for Protection in Carbohydrate Chemistry. Part 18. Allyl and Benzyl Ethers of myo-Inositol. Intermediates for the Synthesis of myo-Inositol Triphosphates
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Racemic 1,2:4,5-di-O-isopropylidene-myo-inositol was converted into racemic 1,2,4-tri-O-benzyl-myo-inositol, 1,2,4-tri-O-p-methoxybenzyl-myo-inositol and 2,4,5-tri-O-benzyl-myo-inositol using allyl groups for 'temporary' protection.The benzyl ethers are required as intermediates for the synthesis of the 'second messenger', inositol 1,4,5-triphosphate and its metabolite, inositol 1,3,4-triphosphate. 1,2,3,4-Tetra-O-benzyl-myo-inositol, and its two monoallyl and monoprop-1-enyl ethers, were also prepared as model compounds for phosphorylation studies of the vicinal 5,6-diol system which occurs in 1,2,4-tri-O-benzyl-myo-inositol.
- Gigg, Jill,Gigg, Roy,Payne, Sheila,Conant, Robert
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p. 423 - 430
(2007/10/02)
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- MICROBIAL OXIDATION IN SYNTHESIS: A SIX STEP PREPARATION OF (+/-)-PINITOL FROM BENZENE
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Synthesis of (+/-)-pinitol in 35percent overall yield from benzene has been achieved where the key step involved microbial oxidation of benzene to cis-1,2-dihydroxycyclohexa-3,5-diene.
- Ley, Steven V.,Sternfeld, Francine,Taylor, Stephen
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p. 225 - 226
(2007/10/02)
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- NOVEL BIOSYNTHESIS OF D-PINITOL IN SIMMONDSIA CHINENSIS
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Chase experiments with 14CO2 and feeding experiments with labwelled inositols showed that D-pinitol in leaves of Simmondsia chinensis arises via epimerization of D-ononitol.This finding represents an alternative pathway, since D-pinitol is formed in gymnosperms and other plants by epimerization of sequoyitol.Key Word Index -- Simmondsia chinensis; Simmondsiaceae; jojoba; biosynthesis; cyclitols; D-pinitol; D-ononitol.
- Dittrich, Peter,Korak, Andrea
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