- Lithium hydride as an efficient reagent for the preparation of 1,2-anhydro inositols: Does the reaction proceed through ‘axial rich’ conformation?
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scyllo-Inositol derived 1,2-trans-diequatorial halohydrins can be efficiently converted to the corresponding epoxides in the presence of lithium hydride. The structure of one of the epoxides was determined by single crystal X-ray diffraction analysis. Thi
- Sarkar, Nitai,Sardessai, Richa S.,Shashidhar, Mysore S.,Tamboli, Majid I.,Gonnade, Rajesh G.
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- Synthesis and in vitro anticancer activity evaluation of novel bioreversible phosphate inositol derivatives
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The chemistry and biology of phosphorylated inositols have become intense areas of research during the last two decades due to their involvement in various cellular signaling processes. However, the metabolic instability by phosphatases or kinases and poo
- Chen, Wenbin,Deng, Zhaohui,Chen, Kuangyu,Dou, Daolei,Song, Fanbo,Li, Luyuan,Xi, Zhen
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supporting information
p. 172 - 181
(2015/03/05)
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- Efficient regioselective protection of myo-inositol via facile protecting group migration
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A cis-1,2-cyclohexanediol, 1,4,5,6-tetra-O-benzyl-myo-inositol, was selectively protected at the axial C2-hydroxyl via acid-mediated rearrangement of the corresponding 1,2-orthoacetate, or via the base-induced migration of a protecting group that had previously been easily installed with complete regioselectivity at the adjacent equatorial hydroxyl. Esters 4a-6a were synthesized in high yields (75-82%) while sulfonate 7a and silyl ether 8a were obtained in 85 and 31% yields, respectively. The migration of the esters induced by DBU results in equilibrium between regioisomers favouring the C2 protected isomer, but NaH induced migration of sulfonyl and silyl groups results in complete migration from equatorial to axial hydroxyl groups.
- Nkambule, Comfort M.,Kwezi, Nomfundo W.,Kinfe, Henok H.,Nokwequ, Mbulelo G.,Gammon, David W.,Oscarson, Stefan,Karlsson, Erik
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p. 618 - 623
(2011/03/19)
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- Relative reactivity of hydroxyl groups in inositol derivatives: role of metal ion chelation
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O-Alkylation of myo-inositol derivatives containing more than one hydroxyl group via their alkali metal alkoxides (sodium or lithium) preferentially occurs at a hydroxyl group having a vicinal cis-oxygen atom. In general the observed selectivity is relatively higher for lithium alkoxides than for the corresponding sodium alkoxide. The observed regioselectivity is also dependent on other factors such as the solvent and reaction temperature. A perusal of the results presented in this article as well as those available in the literature suggests that chelation of metal ions by inositol derivatives plays a significant role in the observed regioselectivity. Steric factors associated with the axial or equatorial disposition of the reacting hydroxyl groups do not contribute much to the outcome of these O-alkylation reactions. These results could serve as guidelines in planning synthetic strategies involving other carbohydrates and their derivatives.
- Devaraj, Subramanian,Jagdhane, Rajendra C.,Shashidhar, Mysore S.
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experimental part
p. 1159 - 1166
(2009/10/04)
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- COMPOUNDS AND COMPOSITIONS FOR THE DETECTION AND TREATMENT OF ALZHEIMER'S DISEASE AND RELATED DISORDERS
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One aspect of the present invention relates to compounds, compositions and methods for diagnosis and/or treatment of a subject suffering from an amyloidosis-associated pathological condition. In certain embodiments, the imaging and/or therapeutic agents of the instant invention may be administered to a subject for identification and/or treatment of amyloid deposits. A specific imaging method detects amyloid deposits by administering the imaging agent to the subject and detecting the spatial distribution of the agent. Differential accumulation of the agent is indicative of AD or an amyIoidosis-associated pathological condition and can be monitored by using a PET or SPECT camera.
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- Achievement of ring inversion of myo-inositol derivatives due to silyloxy/silyloxy repulsion enhanced by the trans-substituents on both sides
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The introduction of quite bulky trialkyl or diarylalkylsilyl groups into vicinal trans-hydroxy groups induced a conformational flip of certain multifunctionalized cyclohexane rings from the usual chair form possessing more equatorial substituents (equatorial-rich chair form) into another chair-form that has more axial substituents (axial-rich chair form). This realization was experimentally revealed by the conformational study of the synthetic myo-inositol derivatives possessing two tert-butyldimethylsilyl (TBS), two triisopropylsilyl (TIPS), or two tert-butyldiphenylsilyl (TBDPS) groups on an adjacent trans-diol. Among them, the cyclohexane rings of the 4,5-bis-O-TIPS-myo-inositol, 4,5-bis-O-TBDPS-myo-inositol, and 1,2,3,6-tetra-O-benzyl-4,5-bis-O-TBDPS-myo-inositol were in the axial-rich chair form. Comparison of the ring conformations also revealed that the order of the repulsion was OTBDPS/OTBDPS>OTIPS/OTIPS>OTBS/OTBS, and the silyloxy/silyloxy repulsion was enhanced when the two silyloxy groups were placed in the center of the contiguous four equatorial substituents.
- Okajima, Kotaro,Mukae, Tatsuya,Imagawa, Hiroshi,Kawamura, Yoshiaki,Nishizawa, Mugio,Yamada, Hidetoshi
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p. 3497 - 3506
(2007/10/03)
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- INOSITOL-BASED MOLECULAR TRANSPORTERS AND PROCESSES FOR THE PREPARATION THEREOF
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Inositol derivatives in accordance with the present invention are effective in significantly enhancing the transportation of various therapeutic molecules across a biological membrane, which may include the plasma membrane, nuclear membrane or blood-brain barrier.
- -
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Page/Page column 23
(2008/06/13)
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- Stable axial-rich chair conformer of myo-inositol derivatives due to introduction of two adjacent bulky silyl protections
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The ring-conformational change of myo-inositol derivatives by introducing two tert-butyldimethylsilyl, triisopropylsilyl, or tert-butyldiphenylsilyl groups into the 1,2-trans hydroxy groups - 3,4- and 4,5-positions - were investigated. The cyclohexane cores of the 4,5-bis-O-silylated derivatives with tert-butyldiphenylsilyl or triisopropylsilyl groups were present in the axial-rich chair form.
- Yamada, Hidetoshi,Okajima, Kotaro,Imagawa, Hiroshi,Mukae, Tatsuya,Kawamura, Yoshiaki,Nishizawa, Mugio
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p. 3157 - 3160
(2007/10/03)
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- Syntheses of penta-O-benzyl-myo-inositols, O-β-L-arabinosyl-(1 → 2)sn-myo-inositol, O-α-D-galactosyl-(1 → 3)-sn-myo-inositol, and O-α-D-galactosyl-(1 → 6)-O-α-D-galactosyl-(1 → 3)-sn-myo-inositol
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Two-step conversions of myo-inositol into (±)-2,3,4,5,6- and 1,3,4,5,6-penta-O-benzyl-myo-inositols are described. Starting from these monohydroxy derivatives of myo-inositol, O-β-L-arabinopyranosyl-(1→2)-sn-myo-inositol from Japanese green tea, Camellia sinensis, and O-α-D-galactopyranosyl-(1→3)-sn-myo-inositol (galactinol) as well as its homolog, O-α-D-galactopyranosyl-(1→6(II))-galactinol, were synthesized by way of the in situ activating glycosylation procedure.
- Koto,Hirooka,Yoshida,Takenaka,Nagamitsu,Sakurai,Zen,Yago,Tomonaga
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p. 2521 - 2529
(2007/10/03)
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- Synthesis of all possible regioisomers of scyllo-inositol phosphate
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scyllo-Inositol is the all equatorial stereoisomer of myo-inositol. All possible 12 regioisomers of scyllo-inositol phosphate were synthesized for the first time via a scyllo-inositol benzoate intermediate, which was derived from a myo-inositol derivative. The stereoinversion of myo-inositol into scyllo-inositol was accomplished by Mitsunobu reaction of the vicinal cis- diol. The requisite intermediates, scyllo-inositol benzoates were obtained by benzoyl migration or random benzoylation, and phosphorylated to give scyllo- IP(n). (C) 1999 Elsevier Science Ltd.
- Chung, Sung-Kee,Kwon, Yong-Uk,Chang, Young-Tae,Sohn, Kwang-Hoon,Shin, Jung-Han,Park, Kyu-Hwan,Hong, Bong-Jin,Chung, In-Hee
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p. 2577 - 2589
(2007/10/03)
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- Practical synthesis of all inositol stereoisomers from myo-inositol
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Synthesis of six inositol stereoisomers was successfully carried out via conduritol intermediates prepared from myo-inositol. Dihydroxylation and epoxidation followed by ring opening of the conduritol B, C and F derivatives gave epi-, allo-, muco-, neo-, DL-chiro- and scyllo-inositol. The cis- inositol derivative, which may not be prepared by this approach, was synthesized in 5 steps via 2-O-benzoyl-myo-inositol orthoformate as the key intermediate.
- Chung, Sung-Kee,Kwon, Yong-Uk
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p. 2135 - 2140
(2007/10/03)
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- Membrane-permeant analogues of the putative second messenger myo-inositol 3,4,5,6-tetrakisphosphate
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For future investigations of the binding properties of D-myo-inositol 3,4,5,6- and 1,4,5,6-tetrakis-phosphate [D-Ins(3,4,5,6)P4 and D-Ins(1,4,5,6)P4, respectively] to their putative target proteins, a set of analogues with modificati
- Roemer, Stefan,Stadler, Christoph,Rudolf, Marco T.,Jastorff, Bernd,Schultz, Carsten
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p. 1683 - 1694
(2007/10/03)
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- Synthesis of novel vitamin C phosphodiesters: Stability and antioxidant activity
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A novel series of hybrid L-ascorbic acid (vitamin C) phosphodiesters linked at the C-2 hydroxyl group with other biologically active substances, namely myo-inositol, arbutin, 4-hydroxy-L-proline, and glycolic acid were synthesized, and their thermal stability and reducing activity against free radicals were estimated in vitro. All of the phosphodiesters exhibited high thermal stabilities; however, their antioxidant activities in vitro were generally lower than that of vitamin C.
- Morisaki, Kazuo,Ozaki, Shoichiro
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p. 123 - 138
(2007/10/03)
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- Syntheses of novel hybrid vitamin C derivatives: Stability and biological activity
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A novel series of hybrid L-ascorbic acid (vitamin C) derivatives linking other biologically active substances glycolic acid, myo-inositol, and α-tocopherol (vitamin E) at the C-2 or C-3 hydroxyl group were synthesized, and their thermal stability and inhibitory activities against tyrosinase-catalyzed melanin formation, active oxygen species (AOS), and free radicals were evaluated in vitro. Among these derivatives, 2-O-carboxymethylascorbic acid had high thermal stability as well as moderate inhibitory activities against tyrosinase-catalyzed melanin formation, AOS, and free radicals compared to other typical inhibitors and scavengers. On the other hand, 3-O-carboxymethylascorbic acid was markedly unstable in aqueous solution. The 2-O-carbonylmethyl derivatives linking myo-inositol or vitamin E were susceptible to degrading, however the vitamin E derivative had stronger inhibitory activities against AOS and free radicals than free vitamin C.
- Morisaki, Kazuo,Ozaki, Shoichiro
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p. 725 - 734
(2007/10/03)
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- Synthesis of (±) 1,2-dideoxy-1,2-diamino-myo-inositol
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Starting from myo-inositol, an isostere, diaminated in positions 1 and 2, was prepared. The key step of the synthesis was the simultaneous inversion of the dimesylate 6 with sodium azide leading to the global retention of the configuration.
- Guedat, Philippe,Spiess, Bernard,Schlewer, Gilbert
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p. 7375 - 7378
(2007/10/02)
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- Synthesis and Tritium Radiolabelling of Fluorinated Analogues of myo-Inositol
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Syntheses have been developed for a set of six myo-inositol analogues from myo-inositol in which single hydroxy groups have been replaced by fluorine (monodeoxy-fluoro-myo-inositols).Except for 2-deoxy-2-fluoro-myo-inositol 32 and 1D-4-deoxy-4-fluoro-myo-
- Offer, John L.,Voorheis, H. Paul,Metcalfe, James C.,Smith, Gerry A.
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p. 953 - 960
(2007/10/02)
-
- Total Synthesis of Fluorinated Analogues of Inositol and Inositol 1,4,5-Trisphosphate
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Syntheses of fluorinated analogues of inositol and inositol 1,4,5-trisphosphate are described. 1-Deoxy-1-fluoro-scyllo-inositol, 2-deoxy-2,2-difluoro-myo-inositol, DL-2-deoxy-2-fluoro-scyllo-inositol 1,4,5-trisphosphate and DL-2-deoxy-2,2-difluoro-myo-ino
- Sawyer, Deborah A.,Potter, Barry V. L.
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p. 923 - 932
(2007/10/02)
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- Lewis acid-catalysed rearrangement of myo-inositol orthoformate derivatives
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Reduction of 2,4,6-tri-O-benzyl-DL-myo-inositol 1,3,5-orthoformate (1) with di-isobutylaluminium hydride gave 2,4,6-tri-O-benzyl-1,3-O-methylene-DL-myo-inositol (2), whereas reaction with trimethylaluminium gave 2,4,6-tri-O-benzyl-1,5-O-ethylidene-DL-myo-
- Gilbert, Ian H.,Holmes, Andrew B.,Pestchanker, Mauricio J.,Young, Rodney C.
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p. 117 - 130
(2007/10/02)
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- Synthesis of D- and L-myo-Inositol 1-phosphorothioate, Substrates for Inositol Monophosphatase
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The D- and L- enantiomers of myo-inositol 1-phosphorothioate have been synthesized from 2,3,4,5,6-pentakis-O-benzyl myo-inositol in 6 steps, both compounds are substrates for inositol monophosphatase.D-glucopyranose 6-phosphorothioate did not serve as a s
- Baker, Graham R.,Billington, David C.,Gani, David
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p. 3895 - 3908
(2007/10/02)
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- AN APPROACH TOWARD THE SYNTHESIS OF RACEMIC MYO-INOSITOL 1-( 3,4-DI-PALMITOYLOXYBUTYL)-SULFONATE
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Substitution of the triflate function in 1,2-isopropylidene-sn-glycerol 3-trifluoromethanesulfonate by the α-lithio-anion of 2,3,4,5,6-penta-O-benzyl-myo-inositol 1-methanesulfonate afforded, after acid hydrolysis of the acetonide function, followed by pa
- Elle, C. J. J.,Dreef, C. E.,Brounts, D. M.,Marel, G. A. van der,Boom, J. H. van
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-
- Total synthesis of myo-inositol polyphosphates from benzene via conduritol B derivatives
-
The four (±)-myo-inositol phosphates 1,4,5-IP3 (1), 2,4,5-IP3 (15), 1,2,4,5-IP4 (17) and 4,5-IP2 (19) have been synthesised from benzene, using the protected conduritol B (10) as the key intermediate.
- Carless, Howard A. J.,Busia, Kofi
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p. 3449 - 3452
(2007/10/02)
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- The synthesis and resolution of (+/-)-1,5,6-tri-O-benzyl-myo-inositol
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Racemic 1,5,6-O-benzyl-myo-inositol was prepared by five routes and converted into 1,5,6-tri-O-benzyl-2,3-O-isopropylidene-myo-inositol, the camphanates of which were readily separated by chromatography.The absolute configurations of the chiral derivative
- Desai, Trupti,Fernandez-Mayoralas, Alfonso,Gigg, Jill,Gigg, Roy,Payne, Sheila
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p. 105 - 123
(2007/10/02)
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- The synthesis of DL-1-(hexadecanoyloxy)methyl- and 1-O-hexadecanoyl-inositols as potential inhibitors of phospholipase C
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The synthesis of racemic analogues of phosphatidylinositol (PI) and phosphatidylinositol 4,5-bisphosphate (PIP2) starting from myo-inositol is described. Inositol derivatives with and without homologation at C(1) and with and without ionic grou
- James,Massy,Wyss
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p. 1037 - 1057
(2007/10/02)
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- A Synthesis of (-)-1L-1-Deoxy-1-fluoro-myo-inositol; a Compound of Potential Use in sorting out the Phosphatidylinositol Response
-
A synthesis of 1L-1-deoxy-1-fluoro-myo-inositol in optically pure form starting from myo-inositol is reported.
- Kozikowski, Alan P.,Xia, Yan,Rusnak, James M.
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p. 1301 - 1303
(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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- THE ALLYL GROUP FOR PROTECTION IN CARBOHYDRATE CHEMISTRY. PART 21. (+/-)-1,2:5,6- AND (+/-)-1,2:3,4-DI-O-ISOPROPYLIDENE-MYO-INOSITOL. THE UNUSUAL BEHAVIOUR OF CRYSTALS OF (+/-)-3,4-DI-O-ACETYL-1,2,5,6-TETRA-O-BENZYL-MYO-INOSITO ON HEATING AND COOLING: A '
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Racemic 1,2-O-isopropylidene-myo-inositol was converted into a mixture of 1,2:5,6-, 1,2:3,4-, and 1,2:4,5-di-O-isopropylidene-myo-inositols which were resolved by g.l.c.The 1,2:4,5 and 1,2:5,6- isomers were isolated from the mixture as benzoate derivative
- Gigg, Jill,Gigg, Roy,Payne, Sheila,Conant, Robert
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p. 2411 - 2414
(2007/10/02)
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- TOTAL SYNTHESIS OF OPTICALLY ACTIVE MYO-INOSITOL 1,4,5-TRIS(PHOSPHATE)
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Optically active myo-inositol 1,4,5-tris(phosphate) has been synthesized starting from myo-inositol.
- Ozaki, Shoichiro,Watanabe, Yutaka,Ogasawara, Tomio,Kondo, Yoshihisa,Shiotani, Naokazu,et al.
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p. 3157 - 3160
(2007/10/02)
-
- INVESTIGATIONS IN THE FIELD OF ASYMMETRICALLY SUBSTITUTED MYOINOSITOL DERIVATIVES. XXX. REACTION OF 2,3-DIHYDROPYRAN WITH TETRASUBSTITUTED DERIVATIVES OF MYOINOSITOL
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In the reaction of 2,3-dihydropyran with 1(3),4(6),5,6(4)-tetra-O-benzyl- and 1(3),4(6),5,6(4)-tetra-O-acetyl-sn-myoinositols the corresponding mono- and ditetrahydropyranyl ethers are formed.
- Stepanov, A. E.,Sibrikov, Yu. I.,Shvets, V. I.
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p. 1946 - 1950
(2007/10/02)
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