949887-64-3Relevant articles and documents
Synthesis and evaluation of hydroxymethylaminocyclitols as glycosidase inhibitors
Trapero, Ana,Egido-Gabás, Meritxell,Bujons, Jordi,Llebaria, Amadeu
, p. 3512 - 3529 (2015)
Four series of C7N aminocyclitol analogues of glucose were synthesized by stereocontrolled epoxide opening of hydroxyl protected forms of the cyclohexane epoxides cyclophellitol and 1,6-epi-cyclophellitol. The resulting hydroxymethyl substitute
Practical synthesis of (-)-1-amino-1-deoxy-myo-inositol from achiral precursors
Gonzalez-Bulnes, Patricia,Casas, Josefina,Delgado, Antonio,Llebaria, Amadeu
, p. 1947 - 1952 (2008/02/10)
A new synthesis of enantiomerically pure 1-amino-1-deoxy-myo-inositol is reported. The route described employs p-benzoquinone, an achiral compound, as the starting material to give conduritol B tetraacetate in three steps. Kinetic resolution of this compound using a palladium catalyst with a chiral ligand allows access to a conduritol B tetraester in high enantiomeric excess. This compound is transformed into tetrabenzyl conduritol B epoxide, which is regioselectively opened with azide to give the key azidocyclitol. Final transformation into (-)-1-amino-1-deoxy-myo-inositol hydrochloride is achieved in four synthetic steps. This sequence allows the synthesis of this compound in high enantiomeric purity in a semi-preparative scale.
Pd catalyzed kinetic resolution of conduritol B. Asymmetric synthesis of (+)-cyclophellitol
Trost,Hembre
, p. 219 - 222 (2007/10/03)
Enantiomerically pure (+)-cyclophellitol is readily available from benzoquinone employing an asymmetric palladium catalyzed kinetic resolution of racemic conduritol B and a novel easily cleavable pivalate analogue.
