01636nas a2200253   4500008004100000022001400041245015900055210006900214260010600283300001400389490000700403520065300410653001301063653001301076653001501089653002101104653001401125100001901139700002301158700002101181700002401202700002501226856013101251       2005                        eng d  a0040-402000aSulfonate protecting groups. synthesis of O- and C-methylated inositols: D- and L-ononitol, D- and L-laminitol, mytilitol and scyllo-inositol methyl ether0 aSulfonate protecting groups synthesis of O and Cmethylated inosi  aTHE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLANDbPERGAMON-ELSEVIER SCIENCE LTDcMAY  a4437-44460 v613 a<p>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.</p>10aCyclitol10aInositol10aOrthoester10aProtecting group10asulfonate1 aSarmah, M., P.1 aShashidhar, M., S.1 aSureshan, K., M.1 aGonnade, Rajesh, G.1 aBhadbhade, Mohan, M.  uhttps://library.ncl.res.in/content/sulfonate-protecting-groups-synthesis-o-and-c-methylated-inositols-d-and-l-ononitol-d-and-001817nas a2200241   4500008004100000022001400041245013000055210006900185260010600254300001400360490000700374520089400381653001401275653001301289653001301302653001501315653002101330653002401351100002301375700002501398700002701423856012501450       2009                        eng d  a0040-402000aRegioselective O-acylation of myo-inositol 1,3,5-orthoesters: dependence of regioselectivity on the stoichiometry of the base0 aRegioselective Oacylation of myoinositol 135orthoesters dependen  aTHE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLANDbPERGAMON-ELSEVIER SCIENCE LTDcMAR  a2703-27100 v653 a<p>A metal mediated unusual 1-3 acyl migration from C4-O to C2-OH of myo-inositol 1,3,5-orthoformate was observed during the alkylation of racemic 4-O-benzoyl-myo-inositol 1,3,5-orthoformate. This has been exploited for the selective esterification of either the C4(6)-OH or the C2-OH of myo-inositol by varying the amount of the base used. While the use of 1 equiv of the base (sodium hydride or potassium tert-butoxide) for the acylation of myo-inositol orthoesters gives the corresponding C4-ester exclusively, the use of two or more equivalents of base for the same reaction gives the C2-ester exclusively. The relatively higher stability of the alkoxide of racemic 2-O-acyl-myo-inositol 1,3,5-orthoester as compared to the alkoxide of 4-O-acyl-myo-inositol 1,3,5-orthoester is suggested to be responsible for the observed isomerization. (c) 2009 Elsevier Ltd. All rights reserved.</p>10aAcylation10aCyclitol10aInositol10aOrthoester10aRegioselectivity10atransesterification1 aSureshan, Kana, M.1 aDevaraj, Subramanian1 aShashidhar, Mysore, S.  uhttps://library.ncl.res.in/content/regioselective-o-acylation-myo-inositol-135-orthoesters-dependence-regioselectivity-0