68737-75-7Relevant academic research and scientific papers
Enhancing intermolecular benzoyl-transfer reactivity in crystals by growing a "reactive" metastable polymorph by using a chiral additive
Murali, Chebrolu,Shashidhar, Mysore S.,Gonnade, Rajesh G.,Bhadbhade, Mohan M.
, p. 261 - 269 (2009)
Racemic 2,4-di-O-benzoylmyo-inositol-1,3,5-orthoacetate, which normally crystallizes in a monoclinic form (form I, space group P21/n) could be persuaded to crystallize out as a metastable polymorph (form II, space group C2/c) by using a small a
Achieving molecular stability of racemic 4-O-benzyl-myo-inositol-1,3,5- orthoformate through crystal formation
Sardessai, Richa,Krishnaswamy, Shobhana,Shashidhar, Mysore S.
, p. 8010 - 8016 (2013/01/15)
Molecular stability of racemic 4-O-benzyl-myo-inositol-1,3,5-orthoformate, an early intermediate during the synthesis of phosphoinositols, depends on the phase in which it is stored. This orthoformate is stable when stored in the crystalline form or as solution in common organic solvents. The former has eluded chemists since the preparation of this benzyl ether two decades ago. The difficulty in obtaining crystals of this orthoformate is due to the cleavage of the orthoformate moiety during storage in the gummy state. Dimorphs (form I and form II) of crystalline racemic 4-O-benzyl-myo-inositol-1,3,5-orthoformate, were obtained when the gummy sample was stored over extended periods of time. Form I crystals could be obtained consistently, by crystallization of a frozen (-20 °C) solid sample, from a solution of dichloromethane-light petroleum. The two crystal forms display dissimilar patterns of hydrogen bonding and molecular assembly in the solid-state.
Divergent synthesis of all possible optically active regioisomers of myo-inositol mono- and bisphosphates
Seo, Kyung-Chang,Yu, Seok-Ho,Chung, Sung-Kee
, p. 305 - 327 (2008/02/12)
All possible optically active regioisomers of myo-inositol mono- and bisphosphates were synthesized using inositol derivatives suitably protected with various protecting groups (IRns) as key intermediates. A series of procedures including Novozym 435 cata
Stereoselective oxidation of protected inositol derivatives catalyzed by inositol dehydrogenase from Bacillus subtilis
Daniellou, Richard,Phenix, Christopher P.,Tam, Pui Hang,Laliberte, Michael C.,Palmer, David R. J.
, p. 401 - 403 (2007/10/03)
Inositol dehydrogenase (EC 1.1.1.18) from Bacillus subtilis is shown to have a nonpolar cavity adjacent to the active site, allowing racemic protected inositol derivatives such as 4-O-benzyl-myo-inositol to be recognized with very high apparent stereoselectivity.
Flexible stereo- and regioselective synthesis of myo-inositol phosphates (Part 2): Via nonsymmetrical conduritol B derivatives
Podeschwa, Michael A. L.,Plettenburg, Oliver,Altenbach, Hans-Josef
, p. 3116 - 3127 (2007/10/03)
A practical route is described for the preparation of myo-inositol phosphates. Optically pure compounds can be prepared, in both forms, from p-benzoquinone by enzymatic resolution of a diacetoxyconduritol key intermediate. Monosubstituted inositol derivat
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 1D- AND 1L-4-O-BENZYL-myo-INOSITOL, 1D-4-O-α-L-FUCOPYRANOSYL-myo-INOSITOL (IDENTICAL TO A NATURAL GLYCOSIDE), AND 1L-4-O-α-L-FUCOPYRANOSYL-myo-INOSITOL
Garegg, Per J.,Lindberg, Bengt,Kvarnstroem, Ingemar,Svensson, Stefan C. T.
, p. 209 - 216 (2007/10/02)
The α-L-fucopyranosyl-myo-inositol isolated from human urine has been proved to be the 1D-4-O-myo-inositol derivative by unambiguous syntheses of this substance and of the diastereomeric 1L-4-O-myo-inositol derivative.The chiral penta-O-benzoyl-myo-inosit
