266682-69-3Relevant articles and documents
Facile syntheses of all possible diastereomers of conduritol and various derivatives of inositol stereoisomers in high enantiopurity from myo-inositol
Kwon, Yong-Uk,Lee, Changgook,Chung, Sung-Kee
, p. 3327 - 3338 (2007/10/03)
Phosphoinositide-based signaling processes are crucially important in intracellular signal transduction events. Inositol phosphate analogues have been useful in probing the structure-activity relationships between inositol phosphates and biomacromolecules, and in studying biological functions of newly found inositol phosphates. Thus, a systematic and ready access to inositol stereoisomers is highly desirable. And practical and convenient syntheses of conduritols and related compounds are also important because of their biological activities and their synthetic utilities in the preparation of other bioactive molecules. We herein report the first syntheses of all possible diastereomers of conduritol and various derivatives of eight inositol stereoisomers in high enantiopurity from myo-inositol, which involve efficient enzymatic resolution of the intermediates conduritol B and C derivatives, followed by oxidation-reduction or the Mitsunobu reaction, and cis-dihydroxylation in stereo- and regioselective manners.
A general procedure to enantiopure conduritols: Sulfur-mediated synthesis of (+)-conduritol B and (-)-conduritol F derivatives and of (-)- conduritol E and F
Cerè, Vanda,Mantovani, Giuseppe,Peri, Francesca,Pollicino, Salvatore,Ricci, Alfredo
, p. 1225 - 1231 (2007/10/03)
We have demonstrated the generality of a simple procedure, synthesizing enantiomerically pure (+)-conduritol B and (-)conduritol F derivatives, starting from D-mannitol and D-sorbitol, respectively. This method, slightly modified, can also be applied to the synthesis of unprotected conduritols: (- )-conduritol E and (-)-conduritol F were obtained. (C) 2000 Elsevier Science Ltd.
Stereoselective synthesis of carba- and C-glycosyl analogs of fucopyranosides
Carpintero, Mercedes,Jaramillo, Carlos,Fernandez-Mayoralas, Alfonso
, p. 1285 - 1296 (2007/10/03)
Fucopyranoside analogs with methylene groups instead of endo- or exo- anomeric oxygens, carba- and C-fucopyranosides, respectively, were synthesized. For the synthesis of 5a-carba-L-fucose (1) two approaches were studied, which shared a common cyclitol bu