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Journal Article
N. T. Patil, Patil, M. T., Sarkar, N., Gonnade, R. G., and Shashidhar, M. S., Access to enantiomeric organic compounds with potential for synthesis via racemic conglomerates: inositol derivatives as a case in point, Crystal Growth & Design, vol. 21, no. 7, pp. 3786-3797, 2021.
R. Sardessai, Krishnaswamy, S., and Shashidhar, M. S., Achieving molecular stability of racemic 4-O-benzyl-myo-inositol-1,3,5-orthoformate through crystal formation, Crystengcomm, vol. 14, no. 23, pp. 8010-8016, 2012.
R. G. Gonnade and Shashidhar, M. S., Acyl-transfer reactions in molecular crystals: reactivity correlation with crystal structure, Acta Crystallographica A‐Foundation and Advances, vol. 70, p. C771, 2014.
B. P. Gurale, Gonnade, R. G., and Shashidhar, M. S., Chiral crystals from an achiral molecule: 4,6-di-O-benzyl-1,3-O-benzylidene-2-O-(4-methoxybenzyl)-myo-5-inosose, Acta Crystallographica Section C-Crystal Structure Communications, vol. 68, pp. O183-O187, 2012.
N. T. Patil, Shashidhar, M. S., Tamboli, M. I., and Gonnade, R. G., Clues from crystal structures pave the way to access chiral myo-inositol derived versatile synthons: resolution of racemic 4-o-allyl-myo-inositol-1,3,5-orthoesters via corresponding dicamphanates by crystallization, Crystal Growth & Design, vol. 17, no. 10, pp. 5432-5440, 2017.
M. I. Tamboli, Bahadur, V., Gonnade, R. G., and Shashidhar, M. S., Cocrystallization of 2,3-dihydroxynaphthalene with its para-, meta-, and ortho-ditoluates: insight into cocrystal formation and clues for the construction of supramolecular assemblies capable of intermolecular acyl group transfer reactivity, Crystal Growth & Design, vol. 15, no. 3, pp. 1226-1232, 2015.
M. I. Tamboli, Bahadur, V., Gonnade, R. G., and Shashidhar, M. S., Cocrystallization of 2,3-dihydroxynaphthalene with its para-, meta-, and ortho-ditoluates: insight into cocrystal formation and clues for the construction of supramolecular assemblies capable of intermolecular acyl group transfer reactivity (vol 15, pg 12, Crystal Growth & Design, vol. 19, no. 10, p. 5998, 2019.
S. Krishnaswamy, Patil, M. T., and Shashidhar, M. S., Comparison of racemic epi-inosose and (-)-epi-inosose, ACTA Crystallographica Section C-Crystal Structure Communications, vol. 67, pp. O435-O438, 2011.
V. Bahadur, Gonnade, R. G., I. Tamboli, M., Krishnaswamy, S., and Shashidhar, M. S., Construction of two-component chemically reactive supramolecular assemblies-acyl migration reactions in cocrystals of napthalene-2,3-diol and its diesters, ChemPlusChem, vol. 86, no. 8, pp. 1128-1134, 2021.
S. Krishnaswamy and Shashidhar, M. S., Correlation of intermolecular acyl transfer reactivity with noncovalent lattice interactions in molecular crystals: toward prediction of reactivity of organic molecules in the solid state, Journal of Organic Chemistry, vol. 83, no. 7, pp. 3952-3959, 2018.
M. I. Tamboli, Bahadur, V., Gonnade, R. G., and Shashidhar, M. S., Correlation of the solid-state reactivities of racemic 2,4(6)-di-O-benzoyl-myo-inositol 1,3,5-orthoformate and its 4,4 `-bipyridine cocrystal with their crystal structures, Acta Crystallographica Section C-Structural Chemistry, vol. 70, no. Part : 11, p. 1040+, 2014.
M. I. Tamboli, Krishnaswamy, S., Gonnade, R. G., and Shashidhar, M. S., Crystal-to-crystal thermal phase transformation of polymorphs of isomeric 2,3-naphthalene diol ditoluates: mechanism and implications for molecular crystal formation and melting, Crystal Growth & Design, vol. 14, no. 10, pp. 4985-4996, 2014.
R. G. Gonnade, Bhadbhade, M. M., and Shashidhar, M. S., Crystal-to-crystal thermal phase transition amongst dimorphs of hexa-O-p-toluoyl-myo-inositol conserving two-dimensional isostructurality, Crystengcomm, vol. 12, no. 2, pp. 478-484, 2010.
R. G. Gonnade, Bhadbhade, M. M., and Shashidhar, M. S., Crystal-to-crystal transformation amongst dimorphs of racemic 2,6-di-O-(p-halobenzoyl)-myo-inositol 1,3,5-orthoformates that achieves halogen bonding contacts, CrystEngComm, vol. 10, no. 3, pp. 288-296, 2008.
M. I. Tamboli, Karothu, D. Prasad, Shashidhar, M. S., Gonnade, R. G., and Naumov, P., Effect of crystal packing on the thermosalient effect of the pincer-type diester naphthalene-2,3-diyl-bis(4-fluorobenzoate): a new class II thermosalient solid, Chemistry-A European Journal, vol. 24, no. 16, pp. 4133-4139, 2018.
A. Mart and Shashidhar, M. S., Elaboration of the ether cleaving ability and selectivity of the classical pearlman's catalyst [Pd(OH)(2)/C]: concise synthesis of a precursor for a myo-inositol pyrophosphate, Tetrahedron, vol. 68, no. 47, pp. 9769-9776, 2012.
M. I. Tamboli, Krishanaswamy, S., Gonnade, R. G., and Shashidhar, M. S., Engineering crystals that facilitate the acyl-transfer reaction: insight from a comparison of the crystal structures of myo-inositol-1,3,5-orthoformate-derived benzoates and carbonates, ACTA Crystallographica Section C-Structural Chemistry, vol. 72, no. 11, p. 875-+, 2016.
C. Murali, Shashidhar, M. S., Gonnade, R. G., and Bhadbhade, M. M., Enhancing intermolecular benzoyl-transfer reactivity in crystals by growing a ``reactive'' metastable polymorph by using a chiral additive, Chemistry-A European Journal, vol. 15, no. 1, pp. 261-269, 2009.
R. C. Jagdhane and Shashidhar, M. S., Formal synthesis of valiolamine from myo-inositol, Tetrahedron, vol. 67, no. 41, pp. 7963-7970, 2011.
S. Krishnaswamy, Shashidhar, M. S., and Bhadbhade, M. M., Helical preorganization of molecules drives solid-state intermolecular acyl-transfer reactivity in crystals: structures and reactivity studies of solvates of racemic 2,6-Di-O-(4-fluorobenzoyl)-myo-inositol 1,3,5-orthoformate, Crystal Growth & Design, vol. 17, no. 1, pp. 117-126, 2017.
S. Krishnaswamy, Gonnade, R. G., Shashidhar, M. S., and Bhadbhade, M. M., Helical self-assembly of molecules in pseudopolymorphs of racemic 2,6-di-O-(4-halobenzoyl)-myo-inositol 1,3,5-orthoformates: clues for the construction of molecular assemblies for intermolecular acyl transfer reaction, Crystengcomm, vol. 12, no. 12, pp. 4184-4197, 2010.
M. I. Tamboli, Krishnaswamy, S., Gonnade, R. G., and Shashidhar, M. S., Identification of molecular crystals capable of undergoing an acyl-transfer reaction based on intermolecular interactions in the crystal lattice, Chemistry-A European Journal, vol. 19, no. 38, pp. 12867-12874, 2013.
S. S. Dixit and Shashidhar, M. S., Inositol derived crown ethers: effect of auxiliary protecting groups and the relative orientation of crown ether oxygen atoms on their metal ion binding ability, Tetrahedron, vol. 64, no. 9, pp. 2160-2171, 2008.
B. P. Gurale, Shashidhar, M. S., Sardessai, R. S., and Gonnade, R. G., Inositol to aromatics -benzene free synthesis of poly oxygenated aromatics, Carbohydrate Research, vol. 461, pp. 38-44, 2018.
M. S. Shashidhar and Krishnaswamy, S., Intermolecular acyl-transfer reactions in molecular crystals , Accounts of Chemical Research, vol. 52, no. 2, pp. 437-446, 2019.
S. Krishnaswamy, Shashidhar, M. S., and Bhadbhade, M. M., 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, Crystengcomm, vol. 13, no. 9, pp. 3258-3264, 2011.
M. I. Tamboli, Shashidhar, M. S., Gonnade, R. G., and Krishnaswamy, S., Intramolecular cyclization of carbonate and thiocarbonate derivatives of myo-inositol in the solid state: implications for acyl group transfer reactions in molecular crystals, Chemistry-A European Journal, vol. 21, no. 39, pp. 13676-13682, 2015.
C. Murali, Gurale, B. P., and Shashidhar, M. S., Intramolecular hydrogen abstraction in radicals derived from inositol 1,3-acetals: efficient access to cyclitols, European Journal of Organic Chemistry, no. 4, pp. 755-764, 2010.
C. Murali, Shashidhar, M. S., Gonnade, R. G., and Bhadbhade, M. M., Investigating organization of molecules that facilitates intermolecular acyl transfer in crystals: reactivity and x-ray structures of O-benzoyl-myo-inositol 1,3,5-orthoesters, European Journal of Organic Chemsitry, vol. 293, no. 1-3, pp. 1153-1159, 2007.
K. Manoj, Gonnade, R. G., Bhadbhade, M. M., and Shashidhar, M. S., Isostructural molecular strings linked via conserved dipolar (ether) O center dot center dot center dot C=O short contacts in conformational polymorphs of racemic 2,4-di-O-acetyl-6-O-tosyl-myo-inositol 1,3,5-orthoesters, CrystEngComm, vol. 11, no. 6, pp. 1022-1029, 2009.
N. Sarkar, Sardessai, R. S., Shashidhar, M. S., Tamboli, M. I., and Gonnade, R. G., Lithium hydride as an efficient reagent for the preparation of 1,2-anhydro inositols: does the reaction proceed through 'axial rich' conformation?, Carbohydrate Research, vol. 463, pp. 32-36, 2018.
B. P. Gurale, Sardessai, R. S., and Shashidhar, M. S., Myo-Inositol 1,3-acetals as early intermediates during the synthesis of cyclitol derivatives, Carbohydrate Research, vol. 399, no. 4, pp. 8-14, 2014.
R. C. Jagdhane, Patil, M. T., Krishnaswamy, S., and Shashidhar, M. S., Orientation of the beta-hydroxyl group controls the diastereoselectivity during the hydride reduction and grignard reaction of inososes, Tetrahedron, vol. 69, no. 25, pp. 5144-5151, 2013.
R. C. Jagdhane and Shashidhar, M. S., Orthogonally protected cyclohexanehexols by a ``one reaction - one product'' approach: efficient access to cyclitols and their analogs, European Journal of Organic Chemistry, no. 15, pp. 2945-2953, 2010.
A. Mart, Sarkar, N. N., and Shashidhar, M. S., Palladium mediated selective cleavage of benzyl and allyl phosphates: a convenient non-hydrogenolytic method for the synthesis of phosphates and phospholipids., ChemistrySelect, vol. 7, no. 25, p. e202201167, 2022.
M. T. Patil, Krishnaswamy, S., Sarmah, M. P., and Shashidhar, M. S., Protecting group directed stereoselective reduction of an epi-inosose: efficient synthesis of epi-inositol, Tetrahedron Letters, vol. 52, no. 29, pp. 3756-3758, 2011.
B. P. Gurale, Vanka, K., and Shashidhar, M. S., Radical mediated deoxygenation of inositol benzylidene acetals: conformational analysis, DFT calculations, and mechanism, Carbohydrate Research, vol. 351, pp. 26-34, 2012.
K. M. Sureshan, Devaraj, S., and Shashidhar, M. S., Regioselective O-acylation of myo-inositol 1,3,5-orthoesters: dependence of regioselectivity on the stoichiometry of the base, Tetrahedron, vol. 65, no. 13, pp. 2703-2710, 2009.
S. Devaraj, Jagdhane, R. C., and Shashidhar, M. S., Relative reactivity of hydroxyl groups in inositol derivatives: role of metal ion chelation, Carbohydrate Research, vol. 344, no. 10, pp. 1159-1166, 2009.
K. Manoj, Gonnade, R. G., Shashidhar, M. S., and Bhadbhade, M. M., Solvent induced crystallization of 1,2,3,4(6),5-penta-O-acetyl-6(4)-O-[(1S)-10-camphor sulfonyl]-myo-inositol diastereomers associated via weak trifurcated C-H center dot center dot center dot O interactions, CrystEngComm, vol. 14, no. 5, pp. 1716-1722, 2012.
K. Manoj, Gonnade, R. G., Bhadbhade, M. M., and Shashidhar, M. S., Subtle crossover from C-H center dot center dot center dot O to S=O center dot center dot center dot C=O short contacts in the association of diastereomers of 2,4(6)-di-O-benzoyl-6(4)-O-[(1S)-10-camphorsulfonyl]-myo-inositol 1,3,5-orthoformate upon format, Crystal Growth & Design, vol. 6, no. 6, pp. 1485-1492, 2006.
B. P. Gurale, Shashidhar, M. S., and Gonnade, R. G., Synthesis of the aminocyclitol units of (-)-hygromycin a and methoxyhygromycin from myo-inositol, Journal of Organic Chemistry, vol. 77, no. 13, pp. 5801-5807, 2012.
B. P. Gurale, Krishnaswamy, S., Vanka, K., and Shashidhar, M. S., Thermal epimerization of inositol 1,3-benzylidene acetals in the molten state, Tetrahedron, vol. 67, no. 38, pp. 7280-7288, 2011.
S. Krishnaswamy, Gonnade, R. G., Bhadbhade, M. M., and Shashidhar, M. S., Two modes of O-H center dot center dot center dot O hydrogen bonding utilized in dimorphs of racemic 6-O-acryloyl-2-O-benzoyl-myo-inositol 1,3,5-orthoformate, Acta Crystallographica Section C-Crystal Structure Communications, vol. 65, pp. O54-O57, 2009.