141040-63-3Relevant academic research and scientific papers
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
Establishment of the structure of pinpollitol by total synthesis of the proposed putative structures
Sureshan, Kana M.,Murakami, Tomohiro,Watanabe, Yutaka
, p. 769 - 772 (2007/10/03)
Proposed structures of pinpollitol, namely 1,4-di-O-methyl-chiro-inositol and 1,3-di-O-methyl-chiro-inositol, have been synthesized from myo-inositol. Racemic 1,4-di-O-methyl-chiro-inositol has been synthesized from the readily available 1,2:4,5-di-O-isop
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.
General synthesis of 3-phosphorylated mj'o-inositol phospholipids and derivatives
Painter, Gavin F.,Grove, Simon J. A.,Gilbert, Lan H.,Holmes, Andrew B.,Raithby, Paul R.,Hill, Malcolm L.,Hawking, Phillip T.,Stephens, Leonard R.
, p. 923 - 935 (2007/10/03)
The D-3-phosphorylated wyo-inositol phospholipids PtdIns(3)P, PtdIns(3,4)P2, PtdIns(3,4,5)P3 and PtdIns(3,5)P2 were synthesised from /yo-inositol orthoformate 8. Key transformations included the regioselective DIBAL- and trimethylaluminium-mediated cleavages of wiyo-inositol orthoformate intermediates and a resolution-protection protocol using the camphor acetals 17. The final reductive debenzylation was effected with Pearlman's catalyst [Pd(OH)J in the presence of sodium hydrogen carbonate. The biological properties of the phospholipids were evaluated against various protein kinases (PKB and PDK-1) in which they played an important activation role.
Synthesis and Tritium Radiolabelling of Fluorinated Analogues of myo-Inositol
Offer, John L.,Voorheis, H. Paul,Metcalfe, James C.,Smith, Gerry A.
, p. 953 - 960 (2007/10/02)
Syntheses have been developed for a set of six myo-inositol analogues from myo-inositol in which single hydroxy groups have been replaced by fluorine (monodeoxy-fluoro-myo-inositols).Except for 2-deoxy-2-fluoro-myo-inositol 32 and 1D-4-deoxy-4-fluoro-myo-
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
Lewis acid-catalysed rearrangement of myo-inositol orthoformate derivatives
Gilbert, Ian H.,Holmes, Andrew B.,Pestchanker, Mauricio J.,Young, Rodney C.
, p. 117 - 130 (2007/10/02)
Reduction of 2,4,6-tri-O-benzyl-DL-myo-inositol 1,3,5-orthoformate (1) with di-isobutylaluminium hydride gave 2,4,6-tri-O-benzyl-1,3-O-methylene-DL-myo-inositol (2), whereas reaction with trimethylaluminium gave 2,4,6-tri-O-benzyl-1,5-O-ethylidene-DL-myo-
Total synthesis of new 1,5-bissubstituted myo-inositol derivatives. Synthesis of D-myo-inositol 1,5-bisphosphate, 3,5-bisphosphate and of rac. 1,5-Bissulphated and 1,5-bissulphamoylated isosteric analogues
Westerduin, Pieter,Willems, Henrica A. M.,Van Boeckel, Constant A. A.
, p. 6915 - 6918 (2007/10/02)
Convenient synthesis of D-myo-inositol 1,5-bisphosphate, 3,5-bisphosphate and isosteric rac. 1,5-bissulphate and 1,5-bissulphonamide was accomplished from key intermediate 2,3,4,6-tetra-O-benzyl-myo-inositol.
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
