38876-99-2Relevant articles and documents
METHODS OF SYNTHESIS OF SCYLLITOL AND RELATED COMPOUNDS
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Page/Page column 58-61, (2012/05/04)
Methods of synthesis of scyllitol diborate and related compounds are provided, including methods that are performed in all-aqueous solutions. Also provided are methods in which the reaction products are recycled to increase the efficiency of the process. The methods include the steps of conversion of a solution of inositol to scyllitol, conversion of scyllitol in the solution to scyllitol diborate, and isolation of the scyllitol diborate from the solution. The scyllitol diborate is reacted to form substantially pure scyllitol diborate, and the remaining solution is efficiently recycled to scyllitol diborate, then to additional substantially pure scyllitol. This scyllitol diborate recycling step can be applied to a variety of processes to improve the yield of scyllitol. The methods are highly efficient and result in large scale reaction products of high purity.
Efficient syntheses of optically pure chiro- and allo-inositol derivatives, azidocyclitols and aminocyclitols from myo-inositol
Sureshan, Kana M.,Ikeda, Kyoko,Asano, Naoki,Watanabe, Yutaka
, p. 4072 - 4080 (2008/09/20)
Efficient routes for the syntheses of optically pure and hitherto unknown l-chiro- and d-allo-inositol derivatives, azido- and aminocyclitols of l-chiro-configuration, diazido- and diaminocyclitols of d-allo-configuration from economically viable myo-inositol are described. These routes provide access to synthetically flexible 1,2:4,5-di-O-isopropylidene-chiro-inositol and 1,6:3,4-di-O-isopropylidene-allo-inositol, which are otherwise difficult to synthesize directly from their parent inositols. A one pot methodology that allows rapid access to both chiro- and allo-inositol derivatives has also been developed. Investigations on the glycosidase inhibitory properties of these novel azido- and amino-inositols unraveled the potentials of these classes of compounds as novel class of glycosidase inhibitors. Both d and l forms of these cyclitols could be synthesized from myo-inositol in gram scales and hence by exploiting the difference in reactivities of cis- and trans-ketals, a variety of protected derivatives, which are useful for the synthesis of unnatural phosphoinositols and natural products, can be synthesized.
Simple and Efficient Routes to Optically Active chiro- and allo-Inositol Derivatives from myo-Inositol
Sureshan, Kana M.,Watanabe, Yutaka
, p. 493 - 496 (2007/10/03)
Efficient routes for the gram scale syntheses of optically active chiro- and allo-inositol derivatives from readily available 1,2:4,5-di-O- isopropylidene-myo-inositol (1) are described. Both D and L forms of these isomeric inositols could be synthesized from enantiomers of 1. One-pot methodology for the simultaneous synthesis of both chiro and allo has also been developed. The possible selectivity for the cleavage of trans-ketal in presence of the cis is an added advantage for the syntheses of a variety of protected derivatives for phosphoinositol syntheses. These routes provide synthetically flexible 1,2:4,5-di-O-isopropylidene-chiro-inositol and 1,6:3,4-di-O- isopropylidene-allo-inositol which are difficult to achieve otherwise.
L-chiro-inositol derivatives from myo-inositol. Building blocks for inositolphosphoglycans
Cid, M. Belén,Alfonso, Francisco,Martín-Lomas, Manuel
, p. 1370 - 1372 (2007/10/03)
A straightforward synthesis of L-chiro-inositol, deoxy L-chiro-inositol derivatives and L-chiro-inositol building blocks for the preparation of inositolphosphoglycans, is reported from myoinositol. Glycosylation with 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-g
Stereoselective synthesis of myo-, neo-, L-chiro, D-chiro, allo-, scyllo-, and epi-inositol systems via conduritols prepared from p-benzoquinone
Podeschwa, Michael,Plettenburg, Oliver,Vom Brocke, Jochen,Block, Oliver,Adelt, Stephan,Altenbach, Hans-Josef
, p. 1958 - 1972 (2007/10/03)
A practical route is described for the flexible preparation of a wide variety of inositol stereoisomers and their polyphosphates. The potential of this approach is demonstrated by the synthesis of myo-, L-chiro-, D-chiro-, epi-, scyllo-, allo-, and neo-inositol systems. Optically pure compounds in either enantiomeric form can be prepared from p-benzoquinone via enzymatic resolution of a derived conduritol B key intermediate. High-performance anion-exchange chromatography with pulsed amperometric detection permits inositol stereoisomers to be resolved and detected with high sensitivity. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
Stereo- and regiospecificity of yeast phytases-chemical synthesis and enzymatic conversion of the substrate analogues neo- and L-chiro-inositol hexakisphosphate
Adelt, Stephan,Podeschwa, Michael,Dallmann, Guido,Altenbach, Hans-Josef,Vogel, Guenter
, p. 44 - 67 (2007/10/03)
Phytases are enzymes that catalyze the hydrolysis of phosphate esters in myo-inositol hexakisphosphate (phytic acid). The precise routes of enzymatic dephosphorylation by phytases of the yeast strains Saccharomyces cerevisiae and Pichia rhodanensis have been investigated up to the myo-inositol trisphosphate level, including the absolute configuration of the intermediates. Stereoselective assignment of the myo-inositol pentakisphosphates (D-myo-inositol 1,2,4,5,6-pentakisphosphate and D-myo-inositol 1,2,3,4,5-pentakisphosphate) generated was accomplished by a new method based on enantiospecific enzymatic conversion and HPLC analysis. Via conduritol B or E derivatives the total syntheses of two epimers of myo-inositol hexakisphosphate, neo-inositol hexakisphosphate and L-chiro-inositol hexakisphosphate were performed to examine the specificity of the yeast phytases with these substrate analogues. A comparison of kinetic data and the degradation pathways determined gave the first hints about the molecular recognition of inositol hexakisphosphates by the enzymes. Exploitation of the high stereo- and regiospecificity observed in the dephosphorylation of neo- and L-chiro-inositol hexakisphosphate made it possible to establish enzyme-assisted steps for the synthesis of D-neo-inositol 1,2,5,6-tetrakisphosphate, L-chiro-inositol 1,2,3,5,6-pentakisphosphate and L-chiro-inositol 1,2,3,6-tetrakisphosphate.
Novel synthesis of enantiomerically pure natural inositols and their diastereoisomers
Takahashi,Kittaka,Ikegami
, p. 2705 - 2716 (2007/10/03)
The various inositol polyphosphates have been found to trigger many important biological processes. Although the knowledge of this phosphoinositide signaling system has been discovered in the past 10 years, many factors remain unclear. For this reason, there is an increased demand for supplies of D-myo-inositol and particularly of novel analogues to investigate these biological mechanisms in more detail. Herein, we report the efficient syntheses of all diastereoisomers of inositol starting with 6-O-acetyl-5-enopyranosides. Conversion of 6-O-acetyl-5-enopyranosides into the corresponding substituted cyclohexanones (Ferrier-II rearrangement) was found to proceed efficiently with a catalytic amount of palladium dichloride. Stereoselective reduction of β-hydroxy ketones obtained provided the precursors to all inositol diastereoisomers in good to excellent yields and with high stereoselectivities. Good accessibility of these enantiomerically pure inositol diastereoisomers results in the efficient syntheses of D-myo-inositol 1,4,5-trisphosphate and D-myo-inositol 1,3,4,5-tetrakisphosphate.
New syntheses of 1D- and 1L-1,2-anhydro-myo-inositol and assessment of their glycosidase inhibitory activities
Falshaw, Andrew,Hart, Joanne B.,Tyler, Peter C.
, p. 301 - 308 (2007/10/03)
The 1D and 1L enantiomers of 1,2-anhydro-myo-inositol (conduritol B epoxide) were synthesised from 1d-pinitol and 1l-quebrachitol, respectively, and their activities were compared in selected glycosidase inhibition assays. The 1d enantiomer was found to be the active isomer, functioning as an irreversible inhibitor of sweet almond β-D-glucosidase. Neither isomer was active against the α-D-glucosidase from Bacillus stearothermophilus or the β-D-galactosidase from Aspergillus oryzae. (C) 2000 Elsevier Science Ltd.
Transformation of cyclohexene to enantiopure cyclitols mediated by sequential oxyselenenylation with (S,S)-hydrobenzoin: Synthesis of D-chiro-inositol and muco-quercitol
Kim, Kwan Soo,Park, Jong H.,Moon, Hoi Kyung,Yi, Hann
, p. 1945 - 1946 (2007/10/03)
Oxyselenenylation of cyclohexene with (S,S)-hydrobenzoin and subsequent oxidation-elimination allows isolation of an allylic ether in which further phenylselenenylation is completely regioselective, thus allowing entry to the cyclitols D-chiro-inositol and muco-quercitol.
Inositol synthesis: Concise preparation of L-chiro-inositol and muco- inositol from a common intermediate
Brammer Jr., Larry E.,Hudlicky, Tomas
, p. 2011 - 2014 (2007/10/03)
Fully stereoselective large-scale syntheses have been attained for L- chiro-inositol (2) and muco-inositol (3) by means of controlled peripheral oxygenation of cyclohexadiene diol 1.
