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.
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.
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.
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.
