The orientation of the β-hydroxyl group controls the diastereoselectivity during the hydride reduction and Grignard reaction of inososes

[1]  R. Gonnade,et al.  Synthesis of the aminocyclitol units of (-)-hygromycin A and methoxyhygromycin from myo-inositol. , 2012, The Journal of organic chemistry.

[2]  S. Krishnaswamy,et al.  Protecting group directed stereoselective reduction of an epi-inosose: efficient synthesis of epi-inositol , 2011 .

[3]  M. Bhadbhade,et al.  Intermolecular benzoyl group transfer reactivity in crystals of racemic 2,6-di-O-benzoyl-myo-inositol 1,3,5-orthobenzoate: Controlling reactivity by solvate (pseudopolymorph) formation , 2011 .

[4]  V. Laketa,et al.  Photoactivatable and cell-membrane-permeable phosphatidylinositol 3,4,5-trisphosphate. , 2011, Angewandte Chemie.

[5]  B. Kilbas,et al.  Recent advances in inositol chemistry: synthesis and applications , 2011 .

[6]  P. Gaffney,et al.  Synthesis of 4-C-alkyl inositol 1,4,5-trisphosphates and 1,3,4,5-tetrakisphosphates. , 2010, The Journal of organic chemistry.

[7]  M. S. Shashidhar,et al.  Orthogonally Protected Cyclohexanehexols by a “One Reaction – One Product” Approach: Efficient Access to Cyclitols and Their Analogs , 2010 .

[8]  T. Hirokawa,et al.  RCAI-37, 56, 59, 60, 92, 101, and 102, cyclitol and carbasugar analogs of KRN7000: their synthesis and bioactivity for mouse lymphocytes to produce Th1-biased cytokines. , 2009, Bioorganic & medicinal chemistry.

[9]  M. S. Shashidhar,et al.  Relative reactivity of hydroxyl groups in inositol derivatives: role of metal ion chelation. , 2009, Carbohydrate research.

[10]  G. Bultynck,et al.  Regioselective deprotection of orthobenzoates for the synthesis of inositol phosphates. , 2009, Organic & biomolecular chemistry.

[11]  S. Tomoda,et al.  Theoretical study on the mechanism and diastereoselectivity of NaBH4 reduction. , 2009, The journal of physical chemistry. A.

[12]  Anthony L. Spek,et al.  Structure validation in chemical crystallography , 2009, Acta crystallographica. Section D, Biological crystallography.

[13]  C. González‐Bello,et al.  Stereoselective Synthesis of Novel Cyclic γ-Amino Acids and Triazole Derivatives† , 2008 .

[14]  G. Sheldrick.  A short history of SHELX. , 2008, Acta crystallographica. Section A, Foundations of crystallography.

[15]  S. Conway,et al.  Biology-enabling inositol phosphates, phosphatidylinositol phosphates and derivatives. , 2007, Natural product reports.

[16]  M. Bhadbhade,et al.  Sulfonate protecting groups. Synthesis of O- and C-methylated inositols: d- and l-ononitol, d- and l-laminitol, mytilitol and scyllo -inositol methyl ether , 2005 .

[17]  C. Tellier,et al.  Synthesis and glycosidase inhibitory activity of aminocyclitols with a C6- or a C7-ring , 2003 .

[18]  M. S. Shashidhar,et al.  Regioselective protection and deprotection of inositol hydroxyl groups. , 2003, Chemical reviews.

[19]  G. Morris,et al.  Difluorinated analogues of shikimic acid , 2003 .

[20]  M. S. Shashidhar,et al.  Sulfonate protecting groups. Improved synthesis of scyllo-inositol and its orthoformate from myo-inositol. , 2003, Carbohydrate research.

[21]  A. Corsaro,et al.  Intramolecular aldol cyclization of L-lyxo-hexos-5-ulose derivatives: a new diastereoselective synthesis of D-chiro-inositol. , 2002, Bioorganic & medicinal chemistry letters.

[22]  C. Gravier-Pelletier,et al.  New azadisaccharide analogs as potential antidiabetics , 2002 .

[23]  S. Ikegami,et al.  Novel synthesis of enantiomerically pure natural inositols and their diastereoisomers. , 2001, The Journal of organic chemistry.

[24]  R. E. Rosenberg,et al.  An examination of hyperconjugative and electrostatic effects in the hydride reductions of 2-substituted-4-tert-butylcyclohexanones. , 2001, The Journal of organic chemistry.

[25]  T. Katoh,et al.  Enantiocontrolled synthesis of (4S,5S,6S)-6-benzyl-4,5-epoxy-6-hydroxy-2-cyclohexen-1-one, a model compound for the epoxycyclohexenone moiety of scyphostatin , 2000 .

[26]  D. A. Jeyaraj,et al.  The Cation Complexation Model Predicts the Experimental π-Facial Selectivity of 2-ax- and 2-eq-Substituted Cyclohexanones. A Detailed Ab Initio MO Investigation , 2000 .

[27]  S. Danishefsky,et al.  A Highly Stereoselective Total Synthesis of Hispidospermidin: Derivation of a Pharmacophore Model , 2000 .

[28]  Mañas,et al.  Unexpected one-pot epoxy sulfone-enaminone transformation. Synthesis of 5a-carba-beta-mannopyranosylamine , 2000, The Journal of organic chemistry.

[29]  Hideyo Takahashi,et al.  Novel synthesis of enantiomerically pure natural inositols and their diastereomers , 1998 .

[30]  U. Samanta,et al.  Reactivity controlled by lattice interactions in crystal: intermolecular acyl transfer in (±)-2,4-di-O-benzoyl-myo-inositol 1,3,5-orthoformate , 1998 .

[31]  Louis J. Farrugia,et al.  ORTEP-3 for Windows - a version of ORTEP-III with a Graphical User Interface (GUI) , 1997 .

[32]  N. Chida,et al.  Synthesis of acyclic and heterocyclic natural products utilizing cyclitols as novel chiral building blocks , 1997 .

[33]  R. Gigg,et al.  Reactions of the ketone derived from (±)-3,4,5-tri-O-benzyl-1,2-O-isopropylidene-myo-inositol: preparation of racemic derivatives of epi-inositol and of 4-C-methyl-epi- [(±)-iso-laminitol] and 4-C-methyl-myo-inositol [(±)-laminitol] , 1997 .

[34]  B. Potter,et al.  Chemistry of Inositol Lipid Mediated Cellular Signaling , 1995 .

[35]  J. Falck,et al.  Intracellular Mediators: Synthesis of L-.alpha.-Phosphatidyl-D-myo-inositol 3,4,5-Trisphosphate and Glyceryl Ether Analogs , 1995 .

[36]  R. Challiss,et al.  The novel Ins(1,4,5)P3 analogue 3-amino-3-deoxy-Ins(1,4,5)P3: a pH-dependent Ins(1,4,5)P3 receptor partial agonist in SH-SY5Y neuroblastoma cells. , 1994, Journal of medicinal chemistry.

[37]  A. Kozikowski,et al.  Probing the D-1,4,5-IP3/D-1,3,4,5-IP4 functional interface. Synthesis and pharmacology of novel D-3-modified myo-inositol trisphosphate analogues , 1994 .

[38]  T. L. Gall,et al.  Highly regioselective functionalization of a cis-1,2-diol in the myo-inositol series. Application to the synthesis of 2-deoxy-2-mercapto-myo-inositol , 1993 .

[39]  R. Hancock,et al.  A molecular mechanics study of the complexation of metal ions by inositols , 1993 .

[40]  S. Horii,et al.  Synthesis of a branched-chain inosose derivative, a versatile synthon of N-substituted valiolamine derivatives from D-glucose , 1992 .

[41]  S. Horii,et al.  Synthesis of valiolamine and its N-substituted derivatives AO-128, validoxylamine G, and validamycin G via branched-chain inosose derivatives , 1992 .

[42]  S. Ley,et al.  Microbial oxidation in synthesis: preparation of myo-inositol phosphates and related cyclitol derivatives from benzene , 1990 .

[43]  M. D. Turnbull,et al.  Stereochemical control in the synthesis of the cyclohexyl portion of the milbemycin skeleton , 1985 .

[44]  Jack D. Dunitz,et al.  From crystal statics to chemical dynamics , 1983 .

[45]  R. S. Glass,et al.  Highly stereoselective reductions of α-alkoxy-β-keto esters. Aspects of the mechanism of sodium borohydride reduction of ketones in 2-propanol , 1980 .

[46]  J. Dunitz,et al.  Stereochemistry of reaction paths at carbonyl centres , 1974 .

[47]  S. Angyal.  Complex formation between sugars and metal ions , 1973 .

[48]  S. Angyal.  Complexes of carbohydrates with metal cations. I. Determination of the extent of complexing by N.M.R. spectroscopy , 1972 .

[49]  S. Angyal,et al.  Complexing of sugars with metal ions , 1971 .

[50]  C. Warren,et al.  Derivatives of 2,3,4,5,6-penta-O-benzyl-myo-inositol. , 1969, Journal of the Chemical Society. Perkin transactions 1.

[51]  M. Tate,et al.  1282. Cyclitols. Part XXI. Benzyl ethers of myoinositol. Aromatisation of a tosyl derivative of myoinositol , 1965 .

[52]  Ernest L. Eliel,et al.  Stereochemistry of Carbon Compounds , 1962 .

[53]  D. Reymond.  Recherches dans la série des cyclitols XXIII. Sur la réduction de deux inososes par le borohydrure de sodium , 1957 .