01623nas a2200205   4500008004100000022001400041245013900055210006900194260007600263300001400339520079900353653001501152653001401167653001301181653002201194653002101216100002701237700002701264856012601291       2010                        eng d  a1434-193X00aOrthogonally protected cyclohexanehexols by a ``one reaction - one product'' approach: efficient access to cyclitols and their analogs0 aOrthogonally protected cyclohexanehexols by a one reaction one p  aCOMMERCE PLACE, 350 MAIN ST, MALDEN 02148, MA USAbWILEY-BLACKWELLcMAY  a2945-29533 a<p>Differentially protected myo-inositol derivatives were prepared from commercially available myo-inositol through regioselective O-alkylation reactions, which give a single product in each step. These derivatives were converted into six isomeric inositol derivatives carrying orthogonal hydroxy protecting groups. For all these reactions, conditions were chosen to prevent the formation of isomeric products, which obviates the need for separation of isomers and provides the required cyclitol derivative in very good yields. The synthetic potential of these derivatives was illustrated by the conversion of some of the orthogonally protected inositol derivatives into other cyclitol derivatives. Isomeric inositols were also prepared by the global deprotection of all the hydroxy groups.</p>10aAlkylation10acyclitols10aInositol10aProtecting groups10aRegioselectivity1 aJagdhane, Rajendra, C.1 aShashidhar, Mysore, S.  uhttps://library.ncl.res.in/content/orthogonally-protected-cyclohexanehexols-one-reaction-one-product-approach-efficient-001858nas a2200253   4500008004100000022001400041245014000055210006900195260010600264300001400370490000700384520088300391653001301274653002501287653001301312653001301325653001601338653001401354100002701368700002301395700002701418700002701445856013201472       2013                        eng d  a0040-402000aOrientation of the beta-hydroxyl group controls the diastereoselectivity during the hydride reduction and grignard reaction of inososes0 aOrientation of the betahydroxyl group controls the diastereosele  aTHE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLANDbPERGAMON-ELSEVIER SCIENCE LTDcJUN  a5144-51510 v693 a<p>A comparison of the results of the Grignard reaction and the hydride reduction of the carbonyl group of epi- and scyllo-inososes reveals that the extent of diastereoselectivity of these reactions is decided by the orientation of the beta-hydroxyl group (or its derivative). Presence of an axial beta-hydroxyl group generally results in the formation of relatively larger amount of the axial alcohol as a result of the reduction of the carbonyl group. The possible reasons for the observed differences in diastereoselectivity between the reactions of these isomeric epi- and scyllo-inososes have been discussed. The sequence of reactions reported here provides convenient access to C-allcylated inositols, such as iso-laminitol and iso-mytilitol as well as 2-O-methyl epi-inositol, an epimer of the naturally occurring ononitol. (C) 2013 Elsevier Ltd. All rights reserved.</p>10aCyclitol10adiastereoselectivity10aGrignard10aInositol10aNucleophile10areduction1 aJagdhane, Rajendra, C.1 aPatil, Madhuri, T.1 aKrishnaswamy, Shobhana1 aShashidhar, Mysore, S.  uhttps://library.ncl.res.in/content/orientation-beta-hydroxyl-group-controls-diastereoselectivity-during-hydride-reduction-and-0