114297-90-4Relevant articles and documents
Relative reactivity of hydroxyl groups in inositol derivatives: role of metal ion chelation
Devaraj, Subramanian,Jagdhane, Rajendra C.,Shashidhar, Mysore S.
experimental part, p. 1159 - 1166 (2009/10/04)
O-Alkylation of myo-inositol derivatives containing more than one hydroxyl group via their alkali metal alkoxides (sodium or lithium) preferentially occurs at a hydroxyl group having a vicinal cis-oxygen atom. In general the observed selectivity is relatively higher for lithium alkoxides than for the corresponding sodium alkoxide. The observed regioselectivity is also dependent on other factors such as the solvent and reaction temperature. A perusal of the results presented in this article as well as those available in the literature suggests that chelation of metal ions by inositol derivatives plays a significant role in the observed regioselectivity. Steric factors associated with the axial or equatorial disposition of the reacting hydroxyl groups do not contribute much to the outcome of these O-alkylation reactions. These results could serve as guidelines in planning synthetic strategies involving other carbohydrates and their derivatives.
Direct selective and controlled protection of multiple hydroxyl groups in polyols via iterative regeneration of stannylene acetals
Simas, Alessandro B.C.,da Silva, Angelo A.T.,dos Santos Filho, Tarcizio J.,Barroso, Pedro T.W.
supporting information; experimental part, p. 2744 - 2746 (2009/09/25)
A direct selective protection (O-benzylation) of two or more hydroxyl groups in polyols displaying diverse structural patterns was made possible by the establishment of conditions that enable an efficient turnover for the Bu2Sn group, initially
A more convenient and general procedure for O-monobenzylation of diols via Stannylenes: A critical reevaluation of the Bu2SnO method
Simas, Alessandro B. C.,Pais, Karla C.,Da Silva, Angelo A. T.
, p. 5426 - 5428 (2007/10/03)
A more consistent, straightforward, and economical protocol for generation of stannylene species and their reaction with BnBr leading to products of O-monobenzylation of diols has been set. It has shown to be specially indicated for substrates bearing vicinal trans 1,2-diol moieties on cyclohexane backbones, which are more resistant to these transformations. Such protocol has been successfully applied to myo-inositol derivatives and acyclic diols.
The preparation of racemic and enantiomerically pure myo-inositol derivatives as intermediates for the synthesis of phosphatidylinositol 3-, 3,4-bis-, and 3,4,5-tris-phosphates and for the synthesis of analogues of 1D-myo-inositol 1,3,4,5-tetrakisphosphat
Desai, Trupti,Gigg, Jill,Gigg, Roy,Martin-Zamora, Eloisa
, p. 97 - 133 (2007/10/03)
Details of the products obtained by the tin-mediated allylation and benzylation of 1,2-O-isopropylidene-myo-inositol, which were previously described in a preliminary communication, are provided here. Some of the products from these reactions, particularl
The alkylation of dibutylstannylene derivatives of 1,2-O-isopropylidene-myo-inositol
Gigg,Gigg,Martin-Zamora
, p. 2827 - 2830 (2007/10/02)
Benzylation (or allylation) of 1,2-O-isopropylidene-myo-inositol in the presence of an excess of dibutyltin oxide gives, as major products, the readily isolable 3,4,6- (12) and 3,5,6-tri-O-alkyl (13) derivatives which are valuable intermediates for the synthesis of inositol phosphates of the phosphates of the phosphatidylinositol cycle.
The preparation of intermediates for the synthesis of 1D-myo-inositol 1,4,5-triphosphate, a second messenger for signal transduction in cells
Desai, Trupti,Gigg, Jill,Gigg, Roy,Payne, Sheila,Penades, Soledad
, p. 1 - 22 (2007/10/02)
Racemic 1,2,4-tri-O-benzyl-5,6-O-isopropylidene-myo-inositol was prepared by a new route involving crotyl (but-2-enyl) ethers and converted into (-)-ω-camphanates to give the pure crystalline 1L-diastereoisomer and the chirally impure, syrupy 1D-diastereo
The preparation, resolution, and phosphorylation of some benzyl ethers of myo-inositol: Intermediates for the synthesis of myo-inositol phosphates of the phosphatidylinositol cycle
Desai,Gigg,Gigg,Payne
, p. 209 - 228 (2007/10/02)
The syntheses of the following chiral compounds are described: 1D-2,3,6-tri-, 1D-2,4,5-tri, 1D-2,5,6-tri-, 1D-1,2,3,4-tetra, 1D-1,2,3,6-tetra-, 1D-1,2,4,5-tetra-, and 1D-2,3,5,6-tetra-0-benzyl-myo-inositol; and 1D-2,5,6-tri-0-benzyl-1-0-p-methoxybenyl- an
New tetherable derivatives of myo-inositol 2,4,5- and 1,3,4-trisphosphates
Marecek, James F.,Estevez, Virginia A.,Prestwich, Glenn D.
, p. 65 - 74 (2007/10/02)
(+/-)-myo-Inositol 1-(3-aminopropyl hydrogen phosphate) 3,4-bis(disodium phosphate) (5) and (+/-)-myo-inositol 2-(3-aminopropyl hydrogen phosphate) 4,5-bis(disodium phosphate) (11) have been synthesized by convential procedures.Each derivative has been im
The synthesis and resolution of (+/-)-1,5,6-tri-O-benzyl-myo-inositol
Desai, Trupti,Fernandez-Mayoralas, Alfonso,Gigg, Jill,Gigg, Roy,Payne, Sheila
, p. 105 - 123 (2007/10/02)
Racemic 1,5,6-O-benzyl-myo-inositol was prepared by five routes and converted into 1,5,6-tri-O-benzyl-2,3-O-isopropylidene-myo-inositol, the camphanates of which were readily separated by chromatography.The absolute configurations of the chiral derivative
FLUORINATED ANALOGS AND TRITIATED ENANTIOMERS OF INOSITOL (1,3,4)-TRISPHOSPHATE
Boehm, Marcus F.,Prestwich, Glenn D.
, p. 5217 - 5220 (2007/10/02)
The total syntheses of 2-fluoro- and 2,2-difluoro-2-deoxy analogs of DL-myo-Ins(1,3,4)P3 are described.Resolution of a key intermediate followed by borotritide reduction and phosphorylation provided both D- and L--Ins(1,3,4)P3 enantiomers with spe
