메뉴 건너뛰기




Volumn 78, Issue 6, 2013, Pages 2275-2288

Regioselective opening of myo-inositol orthoesters: Mechanism and synthetic utility

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; DEUTERIUM; ESTERS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SUGARS;

EID: 84875161467     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo3027774     Document Type: Article
Times cited : (15)

References (39)
  • 1
    • 0035347166 scopus 로고    scopus 로고
    • Back in the water: The return of the inositol phosphates
    • DOI 10.1038/35073015
    • Irvine, R. F.; Schell, M. J. Back in the Water: The Return of the Inositol Phosphates Nature Rev. Mol. Cell Biol. 2001, 2, 327-338 (Pubitemid 33674045)
    • (2001) Nature Reviews Molecular Cell Biology , vol.2 , Issue.5 , pp. 327-338
    • Irvine, R.F.1    Schell, M.J.2
  • 2
    • 39049186795 scopus 로고    scopus 로고
    • Inositol Phosphates and Phosphoinositides in Health and Disease. Biology of Inositols and Phosphoinositides
    • Shi, Y.; Azab, A. N.; Thompson, M. N.; Greenberg, M. L. Inositol Phosphates and Phosphoinositides in Health and Disease. Biology of Inositols and Phosphoinositides Subcell. Biochem. 2006, 39, 265-292
    • (2006) Subcell. Biochem. , vol.39 , pp. 265-292
    • Shi, Y.1    Azab, A.N.2    Thompson, M.N.3    Greenberg, M.L.4
  • 3
    • 34547102761 scopus 로고    scopus 로고
    • Biology-enabling inositol phosphates, phosphatidylinositol phosphates and derivatives
    • DOI 10.1039/b407701f
    • Conway, S. J.; Miller, G. J. Biology-Enabling Inositol Phosphates, Phosphatidylinositol Phosphates and Derivatives Nat. Prod. Rep. 2007, 24, 687-707 (Pubitemid 47106911)
    • (2007) Natural Product Reports , vol.24 , Issue.4 , pp. 687-707
    • Conway, S.J.1    Miller, G.J.2
  • 4
    • 79952440635 scopus 로고    scopus 로고
    • Recent Advances in Inositol Chemistry: Synthesis and Applications
    • Kilbaş, B.; Balci, M. Recent Advances in Inositol Chemistry: Synthesis and Applications Tetrahedron 2011, 67, 2355-2389
    • (2011) Tetrahedron , vol.67 , pp. 2355-2389
    • Kilbasì, B.1    Balci, M.2
  • 5
    • 33748224042 scopus 로고
    • Chemistry of Inositol Lipid-Mediated Cellular Signaling
    • Potter, B. V. L.; Lampe, D. Chemistry of Inositol Lipid-Mediated Cellular Signaling Angew. Chem., Int. Ed. Engl. 1995, 34, 1933-1972
    • (1995) Angew. Chem., Int. Ed. Engl. , vol.34 , pp. 1933-1972
    • Potter, B.V.L.1    Lampe, D.2
  • 6
    • 0028033234 scopus 로고
    • Molecular-Interactions of Endogenous d - Myo -Inositol Phosphates with the Intracellular d - Myo -Inositol 1,4,5-Trisphosphate Recognition site
    • Lu, P. J.; Gou, D. M.; Shieh, W. R.; Chen, C. S. Molecular-Interactions of Endogenous d-myo -Inositol Phosphates with the Intracellular d-myo -Inositol 1,4,5-Trisphosphate Recognition site Biochemistry 1994, 33, 11586-11597
    • (1994) Biochemistry , vol.33 , pp. 11586-11597
    • Lu, P.J.1    Gou, D.M.2    Shieh, W.R.3    Chen, C.S.4
  • 7
    • 22544466436 scopus 로고    scopus 로고
    • Flexible stereo- and regioselective synthesis of myo-inositol phosphates (part 1): Via symmetrical conduritol B derivatives
    • DOI 10.1002/ejoc.200400911
    • Podeschwa, M. A. L.; Plettenburg, O.; Altenbach, H. J. Flexible Stereo- and Regioselective Synthesis of myo -Inositol Phosphates (Part 1): Via Symmetrical Conduritol B Derivatives Eur. J. Org. Chem. 2005, 3101-3115 (Pubitemid 41018430)
    • (2005) European Journal of Organic Chemistry , Issue.14 , pp. 3101-3115
    • Podeschwa, M.A.L.1    Plettenburg, O.2    Altenbach, H.-J.3
  • 8
    • 3242727747 scopus 로고    scopus 로고
    • Regioselective protection of myo-inositol orthoesters - Recent developments
    • Shashidhar, M. S. Regioselective Protection of myo -Inositol Orthoesters-Recent Developments ARKIVOC 2002, VII, 63-75 (Pubitemid 38957343)
    • (2002) Arkivoc , vol.2002 , Issue.7 , pp. 63-75
    • Shashidhar, M.S.1
  • 9
    • 0345134721 scopus 로고    scopus 로고
    • Regioselective Protection and Deprotection of Inositol Hydroxyl Groups
    • Sureshan, K. M.; Shashidhar, M. S.; Praveen, T.; Das, T. Regioselective Protection and Deprotection of Inositol Hydroxyl Groups Chem. Rev. 2003, 103, 4477-4503
    • (2003) Chem. Rev. , vol.103 , pp. 4477-4503
    • Sureshan, K.M.1    Shashidhar, M.S.2    Praveen, T.3    Das, T.4
  • 10
    • 0035897166 scopus 로고    scopus 로고
    • Sulfonate protecting groups. Regioselective O-sulfonylation of myo-inositol orthoesters
    • DOI 10.1016/S0040-4039(01)00364-1, PII S0040403901003641
    • Sureshan, K. M.; Shashidhar, M. S. Sulfonate Protecting Groups. Regioselective O -Sulfonylation of myo -Inositol Orthoesters Tetrahedron Lett. 2001, 42, 3037-3039 (Pubitemid 32276039)
    • (2001) Tetrahedron Letters , vol.42 , Issue.16 , pp. 3037-3039
    • Sureshan, K.M.1    Shashidhar, M.S.2
  • 12
    • 0027116057 scopus 로고
    • Lewis Acid Catalysed Rearrangements of myo -Inositol Orthoformate Derivatives
    • Gilbert, I. H.; Holmes, A. B.; Pestchanker, M. J.; Young, R. C. Lewis Acid Catalysed Rearrangements of myo -Inositol Orthoformate Derivatives Carbohydr. Res. 1992, 234, 117-130
    • (1992) Carbohydr. Res. , vol.234 , pp. 117-130
    • Gilbert, I.H.1    Holmes, A.B.2    Pestchanker, M.J.3    Young, R.C.4
  • 15
    • 0001013850 scopus 로고    scopus 로고
    • Chelation-Assisted C-O Bond Cleavage of Ortho Esters. A Convenient Synthesis of myo-Inositol Derivatives Having Free Hydroxy Group(s) at Specific Position(s)
    • Yeh, S. M.; Lee, G. H.; Wang, Y.; Luh, T. Y. Chelation-Assisted C-O Bond Cleavage of Ortho Esters. A Convenient Synthesis of myo -Inositol Derivatives Having Free Hydroxy Group(s) at Specific Position(s) J. Org. Chem. 1997, 62, 8315-8318 (Pubitemid 128497049)
    • (1997) Journal of Organic Chemistry , vol.62 , Issue.24 , pp. 8315-8318
    • Yeh, S.-M.1    Lee, G.H.2    Wang, Y.3    Luh, T.-Y.4
  • 16
    • 0030767355 scopus 로고    scopus 로고
    • Rapid Synthesis of the Enantiomers of myo -Inositol-1,3,4,5- Tetrakisphosphate by Direct Chiral Desymmetrization of myo -Inositol Orthoformate
    • Riley, A. M.; Mahon, M. F.; Potter, B. V. L. Rapid Synthesis of the Enantiomers of myo -Inositol-1,3,4,5-Tetrakisphosphate by Direct Chiral Desymmetrization of myo -Inositol Orthoformate Angew. Chem., Int. Ed. Engl. 1997, 36, 1472-1474
    • (1997) Angew. Chem., Int. Ed. Engl. , vol.36 , pp. 1472-1474
    • Riley, A.M.1    Mahon, M.F.2    Potter, B.V.L.3
  • 17
    • 33845376826 scopus 로고
    • Synthesis of Mono and Unsymmetrical Bis Ortho-esters of scyllo -Inositol
    • Lee, H. W.; Kishi, Y. Synthesis of Mono and Unsymmetrical Bis Ortho-esters of scyllo -Inositol J. Org. Chem. 1985, 50, 4402-4404
    • (1985) J. Org. Chem. , vol.50 , pp. 4402-4404
    • Lee, H.W.1    Kishi, Y.2
  • 19
    • 0035864884 scopus 로고    scopus 로고
    • Convenient synthesis of 4,6-di-O-benzyl-myo-inositol and myo-inositol 1,3,5-orthoesters
    • DOI 10.1016/S0008-6215(00)00296-2, PII S0008621500002962
    • Praveen, T.; Shashidhar, M. S. Convenient Synthesis of 4,6-Di- O -benzyl- myo -Inositol and myo -Inositol 1,3,5-Orthoesters Carbohydr. Res. 2001, 330, 409-411 (Pubitemid 32206410)
    • (2001) Carbohydrate Research , vol.330 , Issue.3 , pp. 409-411
    • Praveen, T.1    Shashidhar, M.S.2
  • 20
    • 0034729463 scopus 로고    scopus 로고
    • Sulfonate Protecting Groups. Regioselective O -Acylation of myo -Inositol 1,3,5-Orthoesters: The Role of Acyl Migration
    • Sureshan, K. M.; Shashidhar, M. S. Sulfonate Protecting Groups. Regioselective O -Acylation of myo -Inositol 1,3,5-Orthoesters: The Role of Acyl Migration Tetrahedron Lett. 2000, 41, 4185-4188
    • (2000) Tetrahedron Lett. , vol.41 , pp. 4185-4188
    • Sureshan, K.M.1    Shashidhar, M.S.2
  • 21
    • 32444445836 scopus 로고    scopus 로고
    • Chiral desymmetrisation of myo-inositol 1,3,5-orthobenzoate gives rapid access to precursors for second messenger analogues
    • DOI 10.1016/j.tetasy.2005.12.008, PII S0957416605009870
    • Riley, A. M.; Godage, H. Y.; Mahon, M. F.; Potter, B. V. L. Chiral Desymmetrisation of myo -Inositol 1,3,5-Orthobenzoate Gives Rapid Access to Precursors for Second Messenger Analogues Tetrahedron Asymm. 2006, 17, 171-174 (Pubitemid 43226623)
    • (2006) Tetrahedron Asymmetry , vol.17 , Issue.2 , pp. 171-174
    • Riley, A.M.1    Godage, H.Y.2    Mahon, M.F.3    Potter, B.V.L.4
  • 26
    • 0000804001 scopus 로고    scopus 로고
    • An Advantageous Synthesis of 1D- and 1L-1,2,3,5/4-Cyclohexanepentol
    • Biamonte, M. A.; Vasella, A. An Advantageous Synthesis of 1D- and 1L-1,2,3,5/4-Cyclohexanepentol Helv. Chim. Acta 1998, 81, 688-694 (Pubitemid 128498306)
    • (1998) Helvetica Chimica Acta , vol.81 , Issue.4 , pp. 688-694
    • Biamonte, M.A.1    Vasella, A.2
  • 27
    • 10044250073 scopus 로고    scopus 로고
    • Chelation controlled regiospecific O-substitution of myo-inositol orthoesters: Convenient access to orthogonally protected myo-inositol derivatives
    • DOI 10.1016/j.tet.2004.11.025, PII S0040402004018976
    • Devaraj, S.; Shashidhar, M. S.; Dixit, S. S. Chelation Controlled Regiospecific O -Substitution of myo -Inositol Orthoesters: Convenient Access to Orthogonally Protected myo -Inositol Derivatives Tetrahedron 2005, 61, 529-536 (Pubitemid 39602810)
    • (2005) Tetrahedron , vol.61 , Issue.3 , pp. 529-536
    • Devaraj, S.1    Shashidhar, M.S.2    Dixit, S.S.3
  • 28
    • 0032505203 scopus 로고    scopus 로고
    • L-α-phosphatidyl-D-myo-inositol 3,5-bisphosphate: Total synthesis of a new inositol phospholipid via myo-inositol orthoacetate
    • PII S0040403998014221
    • Riley, A. M.; Potter, B. V. L. l-α-Phosphatidyl- d-myo -Inositol 3,5-Bisphosphate: Total Synthesis of a New Inositol Phospholipid via myo -Inositol Orthoacetate Tetrahedron Lett. 1998, 39, 6769-6772 (Pubitemid 28396635)
    • (1998) Tetrahedron Letters , vol.39 , Issue.37 , pp. 6769-6772
    • Riley, A.M.1    Potter, B.V.L.2
  • 29
    • 25444491503 scopus 로고    scopus 로고
    • Identical molecular strings woven differently by intermolecular interactions in dimorphs of myo-inositol 1,3,5-orthobenzoate
    • DOI 10.1021/cg050272j
    • Bhosekar, G.; Murali, C.; Gonnade, R. G.; Shashidhar, M. S.; Bhadbhade, M. M. Identical Molecular Strings Woven Differently by Intermolecular Interactions in Dimorphs of myo -Inositol 1,3,5-Orthobenzoate Cryst. Growth Des. 2005, 5, 1977-1982 (Pubitemid 41362479)
    • (2005) Crystal Growth and Design , vol.5 , Issue.5 , pp. 1977-1982
    • Bhosekar, G.1    Murali, C.2    Gonnade, R.G.3    Shashidhar, M.S.4    Bhadbhade, M.M.5
  • 30
    • 37049088700 scopus 로고
    • Ortho Esters and Dialkoxycarbenium Ions-Reactivity, Stability, Structure, and New Synthetic Applications
    • Pindur, U.; Müller, J.; Flo, C.; Witzel, H. Ortho Esters and Dialkoxycarbenium Ions-Reactivity, Stability, Structure, and New Synthetic Applications Chem. Soc. Rev. 1987, 16, 75-87
    • (1987) Chem. Soc. Rev. , vol.16 , pp. 75-87
    • Pindur, U.1    Müller, J.2    Flo, C.3    Witzel, H.4
  • 32
    • 0032996670 scopus 로고    scopus 로고
    • On the role of Neighboring Group Participation and Ortho Esters in Beta-Xylosylation: C-13 NMR Observation of a Bridging 2-Phenyl-1,3-dioxalenium Ion
    • Crich, D.; Dai, Z. M.; Gastaldi, S. On the role of Neighboring Group Participation and Ortho Esters in Beta-Xylosylation: C-13 NMR Observation of a Bridging 2-Phenyl-1,3-dioxalenium Ion J. Org. Chem. 1999, 64, 5224-5229
    • (1999) J. Org. Chem. , vol.64 , pp. 5224-5229
    • Crich, D.1    Dai, Z.M.2    Gastaldi, S.3
  • 33
    • 27644488250 scopus 로고
    • Direct Observation of the Reversible Ring-Opening of the Hydrolysis of 3-Phenyl-2,4,10-trioxa-adamantane
    • Lam, P. W. K.; McClelland, R. A. Direct Observation of the Reversible Ring-Opening of the Hydrolysis of 3-Phenyl-2,4,10-trioxa-adamantane J. Chem. Soc., Chem. Commun. 1980, 883-884
    • (1980) J. Chem. Soc., Chem. Commun. , pp. 883-884
    • Lam, P.W.K.1    McClelland, R.A.2
  • 34
    • 33745869613 scopus 로고
    • Hydrolysis of Trioxaadamantane Ortho Esters. 1. Dialkoxycarbocation - Ortho Ester Equilibrium and Acidity Function
    • McClelland, R. A.; Lam, P. W. K. Hydrolysis of Trioxaadamantane Ortho Esters. 1. Dialkoxycarbocation-Ortho Ester Equilibrium and Acidity Function Can. J. Chem. 1984, 62, 1068-1073
    • (1984) Can. J. Chem. , vol.62 , pp. 1068-1073
    • McClelland, R.A.1    Lam, P.W.K.2
  • 35
    • 33745864150 scopus 로고
    • Hydrolysis of Trioxaadamantane Ortho Esters. 2. Kinetic-Analysis and the Nature of the Rate-Determining Step
    • McClelland, R. A.; Lam, P. W. K. Hydrolysis of Trioxaadamantane Ortho Esters. 2. Kinetic-Analysis and the Nature of the Rate-Determining Step Can. J. Chem. 1984, 62, 1074-1080
    • (1984) Can. J. Chem. , vol.62 , pp. 1074-1080
    • McClelland, R.A.1    Lam, P.W.K.2
  • 36
    • 0000511962 scopus 로고
    • Remarkable Stereoselectivity in Hydrolysis of Dioxolenium Ions and Orthoesters Fused to Anchored 6-Membered Rings
    • King, J. F.; Allbutt, A. D. Remarkable Stereoselectivity in Hydrolysis of Dioxolenium Ions and Orthoesters Fused to Anchored 6-Membered Rings Can. J. Chem. 1970, 48, 1754-1769
    • (1970) Can. J. Chem. , vol.48 , pp. 1754-1769
    • King, J.F.1    Allbutt, A.D.2
  • 37
    • 16144363866 scopus 로고    scopus 로고
    • Hydrolysis of cyclic orthoesters: Experimental observations and theoretical rationalization
    • DOI 10.1016/0040-4020(96)00915-5, PII S0040402096009155
    • Li, S. G.; Dory, Y. L.; Deslongchamps, P. Hydrolysis of Cyclic Orthoesters: Experimental Observations and Theoretical Rationalization Tetrahedron 1996, 52, 14841-14854 (Pubitemid 26390897)
    • (1996) Tetrahedron , vol.52 , Issue.47 , pp. 14841-14854
    • Li, S.1    Dory, Y.L.2    Deslongchamps, P.3
  • 38
    • 0003244794 scopus 로고
    • Stereoelectronic Effects in Organic Chemistry
    • In, 1 st ed. Baldwin, J. E. Pergamon Press: Oxford, Vol.
    • Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry. In Organic Chemistry Series, 1 st ed.; Baldwin, J. E., Eds.; Pergamon Press: Oxford, 1983; Vol. 1, pp 82-85.
    • (1983) Organic Chemistry Series , vol.1 , pp. 82-85
    • Deslongchamps, P.1
  • 39
    • 0028298723 scopus 로고
    • Synthesis of 2-substituted myo-inositol 1,3,4,5-tetrakis(phosphate) and 1,3,4,5,6-pentakis(phosphate) analogs
    • DOI 10.1246/bcsj.67.1058
    • Ozaki, S.; Koga, Y.; Ling, L.; Watanabe, Y.; Kimura, Y.; Hirata, M. Synthesis of 2-Substituted myo -Inositol 1,3,4,5-Tetrakis(phosphate) and 1,3,4,5,6-Pentakis(phosphate) Analogs Bull. Chem. Soc. Jpn. 1994, 67, 1058-1063 (Pubitemid 24193109)
    • (1994) Bulletin of the Chemical Society of Japan , vol.67 , Issue.4 , pp. 1058-1063
    • Ozaki, S.1    Koga, Y.2    Ling, L.3    Watanabe, Y.4    Kimura, Y.5    Hirata, M.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.