01468nas a2200181   4500008004100000245015200041210006900193260000800262300001000270490000800280520075300288100001801041700002501059700002701084700002301111700002401134856012801158       2018                        eng d00a Lithium hydride as an efficient reagent for the preparation of 1,2-anhydro inositols: does the reaction proceed through 'axial rich' conformation?0 aLithium hydride as an efficient reagent for the preparation of 1  cJUL  a32-360 v4633 ascyllo-Inositol derived 1,2-trans-diequatorial halohydrins can be efficiently converted to the corresponding epoxides in the presence of lithium hydride. The structure of one of the epoxides was determined by single crystal X-ray diffraction analysis. This provides a potential route for the preparation of ring modified inositol derivatives. DFT calculations suggest that this epoxide formation could be proceeding through the intermediacy of the cyclohexane ring-inverted axial-rich conformer (1,2-trans-diaxial halohydrin). This is supported by the results of DFT calculations on the formation of inositol orthoformate, where the product is locked in the axial-rich conformation, while the starting inositol has the equatorial-rich conformation.1 aSarkar, Nitai1 aSardessai, Richa, S.1 aShashidhar, Mysore, S.1 aTamboli, Majid, I.1 aGonnade, Rajesh, G.  uhttps://library.ncl.res.in/content/lithium-hydride-efficient-reagent-preparation-12-anhydro-inositols-does-reaction-proceed01950nas a2200193   4500008004100000022001400041245014100055210006900196260000800265300001400273490000700287520121800294100002401512700002301536700001801559700002401577700002701601856012801628       2021                        eng d  a1528-748300aAccess to enantiomeric organic compounds with potential for synthesis via racemic conglomerates: inositol derivatives as a case in point0 aAccess to enantiomeric organic compounds with potential for synt  cJUL  a3786-37970 v213 aThe crystal structure database was used to identify inositol derivatives that could be crystallizing as racemic conglomerates. Among the six racemic inositol derivatives identified, racemic 4-O-tosyl-6-O-benzyl-myo-inositol-1,3,5-orthoformate (A) was found to be a true conglomerate and was resolved on the multigram scale by the preferential crystallization technique. This resolution procedure does not require the use of any enantiomeric resolving agent. The resolved enantiomers of A are useful for the synthesis of natural and unnatural enantiomeric derivatives of inositol, since they carry orthogonal hydroxy protecting groups. Racemic 4-O-methanesulfonyl-myo-inositol-1,3,5-orthoformate (B) on crystallization from common organic solvents generally yielded racemic twin crystals, while in the presence of structural analogs as additives, they yielded true racemic crystals. A comparison of the crystal structures of the true racemate, twinned crystal and crystal of one of the enantiomers of B, revealed the reasons for the formation of polymorphic (twin) crystals. Such instances are relatively rarely encountered but nevertheless shed light on our understanding of polymorphism and twinning of crystals.1 aPatil, Nivedita, T.1 aPatil, Madhuri, T.1 aSarkar, Nitai1 aGonnade, Rajesh, G.1 aShashidhar, Mysore, S.  uhttps://library.ncl.res.in/content/access-enantiomeric-organic-compounds-potential-synthesis-racemic-conglomerates-inositol01351nas a2200241   4500008004100000022001400041245004900055210004900104260000800153300001100161490000800172520067100180653002500851653001700876653001300893653001300906653002000919100002400939700001800963700002300981700002401004856008101028       2024                        eng d  a0040-402000aAsymmetric synthesis of inositol derivatives0 aAsymmetric synthesis of inositol derivatives  cAUG  a1341130 v1623 a<p>
	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.</p>
10aAsymmetric synthesis10aCarbohydrate10aCyclitol10aInositol10aNatural product1 aPatil, Nivedita, T.1 aSarkar, Nitai1 aMysore, Shashidhar1 aGonnade, Rajesh, G.  uhttps://library.ncl.res.in/content/asymmetric-synthesis-inositol-derivatives