110550-25-9Relevant academic research and scientific papers
Lithium hydride as an efficient reagent for the preparation of 1,2-anhydro inositols: Does the reaction proceed through ‘axial rich’ conformation?
Sarkar, Nitai,Sardessai, Richa S.,Shashidhar, Mysore S.,Tamboli, Majid I.,Gonnade, Rajesh G.
, p. 32 - 36 (2018/05/22)
scyllo-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. Thi
Conformation inversion of an inositol derivative by use of silyl ethers: A modified route to 3,6-di-O-substituted-L-ido-tetrahydroxyazepane derivatives
Painter, Gavin F.,Falshaw, Andrew,Wong, Herbert
, p. 1007 - 1012 (2007/10/03)
The tans-diequatorial 3,4-diol of 2,5-di-O-benzyl-D-chiro-inositol cleaved selectively with the periodate ion in the presence of the trans-diaxial 1,6-diol to give a dialdehyde (dialdose) from which 3,6-di-O-benzyl-D- mannotetrahydroxyazepane (1) was made. The trans-diaxial 1,6-diol of 3,4-di-O-allyl-2,5-di-O-benzyl-D-chiro-inositol was not cleaved satisfactorily by periodate, but replacement of the allyl substituents with tert-butyldimethylsilyl groups caused conformational inversion of the inositol ring, and the resulting trans-diequatorial 1,6-diol cleaved efficiently to give a dialdehyde from which 3,6-di-O-benzyl-L-tdo-tetrahydroxyazepane (2) can be prepared.
Synthesis and Some Properties of D-myo-Inositol 1,4,5-Tris(dihydrogen phosphate)
Ozaki, Shoichiro,Kondo, Yoshihisa,Shiotani, Naokazu,Ogasawara, Tomio,Watanabe, Yutaka
, p. 729 - 738 (2007/10/02)
Optically active myo-inositol 1,4,5-tris(dihydrogen phosphate) 1, which has now been recognized as a second messenger in a new intracellular signal transduction system, has been prepared starting from myo-inositol.The key step, phosphorylation of an adequately protected polyhydroxy derivative, was accomplished by three methods, among which a phosphoramidite method using a new phosphitylating agent, o-xylylene N,N-diethylphosphoramidite, gave the triphosphoric ester in quantitative yield.Optical resolution was effectively realized by derivatization into diastereoisomeric l-menthoxyacetic esters.NMR spectra and optical rotation are shown to depend on the pH of an aqueous solution of compound 1.
The Allyl Group for Protection in Carbohydrate Chemistry. Part 18. Allyl and Benzyl Ethers of myo-Inositol. Intermediates for the Synthesis of myo-Inositol Triphosphates
Gigg, Jill,Gigg, Roy,Payne, Sheila,Conant, Robert
, p. 423 - 430 (2007/10/02)
Racemic 1,2:4,5-di-O-isopropylidene-myo-inositol was converted into racemic 1,2,4-tri-O-benzyl-myo-inositol, 1,2,4-tri-O-p-methoxybenzyl-myo-inositol and 2,4,5-tri-O-benzyl-myo-inositol using allyl groups for 'temporary' protection.The benzyl ethers are required as intermediates for the synthesis of the 'second messenger', inositol 1,4,5-triphosphate and its metabolite, inositol 1,3,4-triphosphate. 1,2,3,4-Tetra-O-benzyl-myo-inositol, and its two monoallyl and monoprop-1-enyl ethers, were also prepared as model compounds for phosphorylation studies of the vicinal 5,6-diol system which occurs in 1,2,4-tri-O-benzyl-myo-inositol.
Synthesis of Optically Active Inositol Derivatives Starting from D-Glucurono-6,3-lactone
Watanabe, Yutaka,Mitani, Motohiro,Ozaki, Shoichiro
, p. 123 - 126 (2007/10/02)
D-Glucurono-6,3-lactone was converted to optically active and partially protected inositols.The synthetic strategy involves an efficient conversion of the D-gluco configuration to the L-ido configuration and dials to cyclitols.
TOTAL SYNTHESIS OF OPTICALLY ACTIVE MYO-INOSITOL 1,4,5-TRIS(PHOSPHATE)
Ozaki, Shoichiro,Watanabe, Yutaka,Ogasawara, Tomio,Kondo, Yoshihisa,Shiotani, Naokazu,et al.
, p. 3157 - 3160 (2007/10/02)
Optically active myo-inositol 1,4,5-tris(phosphate) has been synthesized starting from myo-inositol.
