@article { ISI:000228607400011, title = {Sulfonate protecting groups. synthesis of O- and C-methylated inositols: D- and L-ononitol, D- and L-laminitol, mytilitol and scyllo-inositol methyl ether}, journal = {Tetrahedron}, volume = {61}, number = {18}, year = {2005}, month = {MAY}, pages = {4437-4446}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, type = {Article}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

Syntheses of D- and L-ononitol, D- and L-laminitol, mytilitol and scyllo-inositol methyl ether starting from myo-imositol are described. One or two of the inyo-inositol 1,3,5-orthoformate hydroxyl groups were protected as tosylates. These mono or ditosylates served as key intermediates for the preparation of O- and C-methyl inositols. Racemic 2,4-di-O-tosyl-myo-inositol 1,3,5-orthoformate was resolved as its diastereomeric camphanates. Use of sulfonate groups for the protection of inositol hydroxyl groups resulted in substantial improvement in the overall yield of O- and C-methyl inositols. (c) 2005 Elsevier Ltd. All rights reserved.

}, keywords = {Cyclitol, Inositol, Orthoester, Protecting group, sulfonate}, issn = {0040-4020}, doi = {10.1016/j.tet.2005.02.073}, author = {Sarmah, M. P. and Shashidhar, M. S. and Sureshan, K. M. and Gonnade, Rajesh G. and Bhadbhade, Mohan M.} } @article {49351, title = {Asymmetric synthesis of inositol derivatives}, journal = {Tetrahedron}, volume = {162}, year = {2024}, month = {AUG}, pages = {134113}, type = {Article}, abstract = {

Both the enantiomers of racemic 4- O -tosyl-6- O -benzyl- myo -inositol-1,3,5-orthoformate ( 2 ) were isolated by preferential crystallization and used to synthesize several enantiomeric myo -inositol derivatives - natural ononitol, natural laminitol, precursors for myo -inositol phosphates and an oxabicyclo [2.2.1] heptane derivative. This work demonstrates the potential of the enantiomeric tosylates D2 and L2 to serve as versatile starting materials for the absolute asymmetric synthesis of inositol derivatives and other natural products from symmetric myo -inositol since no optically active molecular entity was required for the resolution of 2.

}, keywords = {Asymmetric synthesis, Carbohydrate, Cyclitol, Inositol, Natural product}, issn = {0040-4020}, doi = {10.1016/j.tet.2024.134113}, author = {Patil, Nivedita T. and Sarkar, Nitai and Mysore, S. Shashidhar and Gonnade, Rajesh G.} } @article {49699, title = {Desymmetrization of myo-inositol}, journal = {Carbohydrate Research}, volume = {553}, year = {2025}, month = {JUL}, pages = {109505}, type = {Article}, abstract = {

Chemistry and biology of phosphoinositols have been intensely investigated areas of research over the last 4-5 decades due to their involvement in cellular signal transduction pathways. Efficient laboratory synthesis of enantiomeric derivatives of inositols was a central issue since they were required for the delineation of the myo-inositol cycle as well as for the total synthesis of polyol based natural products and their derivatives. This essentially meant the development of competent methods for the desymmetrization of myo-inositol leading to the preparation of enantiomeric O-substituted derivatives of myo-inositol. This was approached by: the classical resolution methods involving separable diastereomers, the chiral pool synthesis, enzyme catalysis, asymmetric catalysis and preferential crystallization of enantiomers in a racemic conglomerate. This review summarizes results obtained in author{\textquoteright}s laboratory, as well as those reported in the literature on attempts at desymmetrization of myo-inositol.

}, keywords = {Conglomerate, Crystallization, Cyclitol, Enantiomers, Inositol, Lipid}, issn = {0008-6215}, doi = {10.1016/j.carres.2025.109505}, author = {Patil, Nivedita T. and Patil, Madhuri T. and Gonnade, Rajesh G. and Shashidhar, Mysore S.} }