๐”– Bobbio Scriptorium
โœฆ   LIBER   โœฆ

Synthesis from quebrachitol of 1l-chiro-inositol 2,3,5-trisphosphate, an inhibitor of the enzymes of 1d-myo-inositol 1,4,5-trisphosphate metabolism

โœ Scribed by Changsheng Liu; Stefan R. Nahorski; Barry V.L. Potter

Publisher
Elsevier Science
Year
1992
Tongue
English
Weight
711 KB
Volume
234
Category
Article
ISSN
0008-6215

No coin nor oath required. For personal study only.

โœฆ Synopsis

t_-Quebrachitol was O-demethylated to give lt_-chiro-inositol which, on treatment with dibutyltin oxide, benzyl chloride, and tetrabutylammonium iodide in acetonitrile, gave mainly crystalline lo-2,3,5tri-0-benzyl-chiro-inositol

(Sal together with lt_-2,3,5,6-tetra-0-benzyl-chiro-inositol. Catalytic hydrogenolysis of the 1,4,6_tribenzoate (6a) of Sa afforded crystalline (-l-lt_-1,4,6-tri-O-benzoyl-chiro-inositol (7). Phosphitylation of 7 with either bis(Zcyanoethyl) N,N-diisopropylphosphoramidite or chlorodiethoxyphosphine followed by oxidation gave the respective 2,3,5-trisphosphate derivatives. Deprotection with either sodium in liquid ammonia or bromotrimethylsilane followed by sodium hydroxide then gave ( -)-lL-chiro-inositol 2,3,5-trisphosphate (2).

๐Ÿ“œ SIMILAR VOLUMES

Synthesis of myo-inositol 1,4,6-trisphos
Synthesis of myo-inositol 1,4,6-trisphosphate, an analogue of myo-inositol 1,4,5-trisphosphate
โœ Yutaka Watanabe; Tomio Ogasawara; Shoichiro Ozaki; Masato Hirata ๐Ÿ“‚ Article ๐Ÿ“… 1994 ๐Ÿ› Elsevier Science ๐ŸŒ English โš– 401 KB

myo-Inositol 1,4,6-u-&phosphate, in optically inactive and active forms, was prepared in order to compare its biological activity with that of myo-inositol 1,3,4,6-tetrakisphosphate which releases Ca2+ from an intracellular store.

Synthesis and Ca2+-release activity of d
Synthesis and Ca2+-release activity of d- and l-myo-inositol 2,4,5-trisphosphate and d- and l-chiro-inositol 1,3,4-trisphosphate
โœ Werner Tegge; Gerald V. Denis; Clinton E. Ballou ๐Ÿ“‚ Article ๐Ÿ“… 1991 ๐Ÿ› Elsevier Science ๐ŸŒ English โš– 767 KB

Partial benzoylation of the 3,4-dibenzyl ethers of D- and L-chiro-inositol provided the 1,2,5-tri-O-benzoyl-3,4-di-O-benzyl-chiro-inositols. Inversion of the free axial hydroxyl group gave a mixture of chiral 1,3,4- and 1,2,4-tri-O-benzoyl-5,6-di-O-benzyl-myo-inositols [W. Tegge and C. E. Ballou, Pr

A chemoenzymatic synthesis of d-myo-inos
A chemoenzymatic synthesis of d-myo-inositol 1,4,5-trisphosphate
โœ Lei Ling; Shoichiro Ozaki ๐Ÿ“‚ Article ๐Ÿ“… 1994 ๐Ÿ› Elsevier Science ๐ŸŒ English โš– 816 KB

Enzyme-catalyzed esterification of racemic 2,3-O-cyclohexylidene-myo-inositol (DL-1) proceeded exclusively in 1,4-dioxane to give optically pure L-1-O-acetyl-2,3-O-cyclohexylidene-myo-inositol (L-2) and D-2,3-O-cyclohexylidene-myo-inositol (D-1). A new practical route has been developed for the synt

Synthesis of (ยฑ)-myo-inositol 1,4,5-tris
Synthesis of (ยฑ)-myo-inositol 1,4,5-trisphosphate and the novel analogue (ยฑ)-myo-inositol 1,4-bisphosphate 5-phosphorothioate
โœ Nicholas J. Noble; Allan M. Cooke; Barry V.L. Potter ๐Ÿ“‚ Article ๐Ÿ“… 1992 ๐Ÿ› Elsevier Science ๐ŸŒ English โš– 758 KB

Novel routes to myo-inositol 1,4,5trisphosphate and a phosphorothioate analogue involving mixed P(V) and P(III) chemistry have been developed. Phosphorylation of 2,3,6-tri-O-benzyl-myo-inositol l-[di-(2,2,2-trichloroethyl) phosphate] with bis(2,2,2-trichloroethyl) phosphorochloridate gave a mixture