98906-25-3Relevant academic research and scientific papers
Synthesis and in vitro anticancer activity evaluation of novel bioreversible phosphate inositol derivatives
Chen, Wenbin,Deng, Zhaohui,Chen, Kuangyu,Dou, Daolei,Song, Fanbo,Li, Luyuan,Xi, Zhen
, p. 172 - 181 (2015/03/05)
The chemistry and biology of phosphorylated inositols have become intense areas of research during the last two decades due to their involvement in various cellular signaling processes. However, the metabolic instability by phosphatases or kinases and poo
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.
Synthesis of the enantiomers of myo-inositol 1,2,4,5-tetrakisphosphate, a regioisomer of myo-inositol 1,3,4,5-tetrakisphosphate
Mills, Stephen J.,Potter, Barry V. L.
, p. 1279 - 1286 (2007/10/03)
Routes for the synthesis of racemic myo-inositol 1,2,4,5-tetrakisphosphate DL-Ins(1,2,4,5)P4 5ab and the chiral antipodes D- and L-myo-inositol 1,2,4,5-tetrakisphosphate 5a and 5b, respectively, are described. For the synthesis of racemate 5ab, 3,6-di-O-benzoyl-1,2:4,5-di-O-isopropylidene-myo-inositol 7ab is prepared in two steps from myo-inositol. The ketals are hydrolysed under acidic conditions to give DL-1,4-di-O-benzoyl-myo-inositol 8ab. Phosphitylation of compounds 8ab using chloro(diethoxy)-phosphine in the presence of base, followed by oxidation and a three-step deprotection strategy, gives DL-Ins(1,2,4,5)P4 5ab. The chiral tetrakisphosphates 5a and 5b are synthesized using a different route. The 4,5-isopropylidene group of DL-3,6-di-O-benzyl-1,2:4,5-di-O-isopropylidene-myo-inositol 13ab are selectively removed under mild acidic conditions to give diol 14ab. p-Methoxybenzylation at the 4,5-positions followed by acid hydrolysis of the cis-isopropylidene ketal affords cis-diol 16ab. Selective coupling of (S)-(+)-O-acetylmandelic acid with diol 16ab at the equatorial hydroxy group provides two diastereoisomers 18 and 19, which are separated by chromatography. Basic hydrolysis of the individual diastereoisomers provides the enantiomers 16a and 16b. Acidic hydrolysis gives D- and L-3,6-di-O-benzyl-myo-inositol 20a and 20b, respectively. Phosphitylation and oxidation of tetraols 20a and 20b gives the fully blocked derivatives, which are deprotected to give tetrakisphosphates 5a and 5b, respectively. The absolute configuration of compound 20a is established by a chemical method. DL-1,2:4,5-Di-O-isopropylidene-myo-inositol 12ab is coupled to (S)-(+)-O-acetylmandelic acid to give a mixture of bis-esters 26 and 27 and crystallisation of the mixture of diastereoisomers affords pure isomer 27. Basic hydrolysis gives the pure enantiomer 12a (for which the absolute configuration is known) and benzylation followed by acid hydrolysis gives tetraol 20a with the same physical properties as compound 20a prepared by a different route described previously. D-Ins(1,2,4,5)P4 5a is a potent mobiliser of intracellular Ca2+ ions in permeabilised platelets, while L-Ins(1,2,4,5)P4 5b is inactive.
Cyclic carbonates as protecting groups in cyclitol chemistry
Desai, Trupti,Gigg, Jill,Gigg, Roy
, p. C5 - C8 (2007/10/03)
Keywords: Cyclic carbonates; Protecting group; ethylene carbonate; Inositol derivatives; myo-Inositol 1,2-carbonate
The synthesis and resolution of (+/-)-1,4-di-O-benzyl-2,3-O-isopropylidene-myo-inositol
Desai, Trupti,Gigg, Jill,Gigg, Roy,Martin-Zamora, Eloisa,Schnetz, Nathalie
, p. 135 - 144 (2007/10/02)
An improved procedure for the preparation of 1,2-O-isopropylidene-myo-inositol is described.Racemic 1,4-di-O-benzyl-2,3-O-isopropylidene-myo-inositol was prepared by tin-mediated benzylation of 1,2-O-isopropylidene-myo-inositol and resolved readily by cry
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 and phosphorylation of 2,5- and 1D-2,6-di-O-benzyl-myo-inositol
Desai,Gigg,Gigg,Payne
, p. 65 - 79 (2007/10/02)
1,3,4,6-Tetra-O-allyl-myo-inositol was converted into the 2,5-di-O-benzyl- and 2,5-di-O-p-methoxybenzyl ethers, and the products were deallylated to give the 2,5-di-O-benzyl (and p-methoxybenzyl) ethers of myo-inositol, which were converted into the mono-
The Allyl Group for Protection in Carbohydrate Chemistry. Part 20. Synthesis of 1L-1-O-Methyl-myo-inositol by Resolution of (+/-)-1,2,4-Tri-O-benzyl-myo-inositol
Gigg, Jill,Gigg, Roy,Payne, Sheila,Conant, Robert
, p. 1757 - 1762 (2007/10/02)
Racemic 1,2,4-tri-O-benzyl-myo-inositol was prepared by two new routes from (+/-)-1,4-di-O-benzyl-5,6-O-isopropylidine-myo-inositol, one route involving the crystalline intermediate (+/-)-1-O-allyl-3,6-di-O-benzyl-4,5-O-isopropylidine-myo-inositol.Oxidati
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.
