114218-23-4Relevant articles and documents
Synthesis of L-scyllo-inositol 1,2,4-trisphosphate, scyllo-inositol 1,2,4,5-tetrakisphosphate and phosphorothioate and DL-2-deoxy-2-fluoro-myo-inositol 1,4,5-trisphosphate: Optical resolution of DL-1-O-allyl-3,6-di-O-benzyl-4,5-O-isopropylidene-scyllo-inositol
Lampe, Dethard,Liu, Changsheng,Mahon, Mary F.,Potter, Barry V. L.
, p. 1717 - 1727 (2007/10/03)
Routes for the synthesis of scyllo-inositol tris- and tetrakis-phosphates and 2-deoxy-2-fluoro-myo-inositol 1,4,5-trisphosphate from myo-inositol have been devised. For DL-scyllo-inositol 1,2,4-trisphosphate, DL-1-O-allyl-3,6-di-O-benzyl-4-5-O-isopropylidene-scyllo-inositol was prepared from the triflate of DL-1-O-allyl-3,6-di-O-benzyl-4,5-O-isopropylidene-myo-inositol by inversion at C-2. Removal of the isopropylidene group and phosphorylation gave the protected trisphosphate. Deblocking with sodium in liquid ammonia afforded racemic scyllo-inositol 1,2,4-trisphosphate. DL-1-O-Allyl-3,6-di-O-benzyl-4,5-O-isopropylidene-scyllo-inositol was resolved into its enantiomers by means of the crystalline 2-O-camphanate ester. The structure of one diastereoisomer, 1D-O-allyl-3,6-di-O-benzyl-2-O-[( - )-camphanoyl]-4,5-O-isopropylidene-scyllo-inositol was determined by single-crystal X-ray crystallography. 1D-( + )-1-O-Allyl-3,6-di-O-benzyl-4,5-O-isopropylidene-scyllo-inositol was used to prepare 1L-( - )-scyllo-inositol 1,2,4-trisphosphate in a fashion analogous to the racemic modification. DL-1-O-Allyl-3,6-di-O-benzyl-scyllo-inositol was isomerised to the (Z)-prop-1-enyl derivative. The propenyl group was then removed to give the meso-1,4-di-O-benzyl-scyllo-inositol. Phosphitylation followed by oxidation or sulfoxidation gave the fully protected tetrakis-phosphate or -phosphorothioate, respectively. After deblocking and purification, scyllo-inositol 1,2,4,5-tetrakisphosphate and scyllo-inositol 1,2,4,5-tetrakisphosphorothioate were obtained. DL-1-O-Allyl-3,6-di-O-benzyl-4,5-O-isopropylidene-scyllo-inositol was isomerised to the 1-O-[(Z)-prop-1-enyl] derivative which was converted into the 2-0-triflate. Displacement of the triflate using tetrabutylammonium fluoride proceeded with inversion of configuration to give DL-3,6-di-O-benzyl-2-deoxy-2-fluoro-4,5-O-isopropylidene-1-O-([(Z)-prop-1-enyl]- myo-inositol. Removal of propenyl and isopropylidene groups afforded DL-3,6-di-O-benzyl-2-deoxy-2-fluoro-myo-inositol, which was phosphitylated and the product oxidised to give the fully protected 2-fluoro trisphosphate. Deprotection furnished DL-2-deoxy-2-fluoro-myo-inositol 1,4,5-trisphosphate. These compounds will be useful probes for investigation of the polyphosphoinositide pathway of cellular signalling.
Synthesis of 2-fluoro-2-deoxy-myo-inositol 1,4,5-trisphosphate and scyllo-inositol 1,2,4-trisphosphate, novel analogues of the second messenger myo-inositol 1,4,5-trisphosphate
Lampe, Dethard,Potter, Barry V. L.
, p. 2365 - 2368 (2007/10/02)
The novel myo-inositol 1,4,5-triphosphate receptor agonists, 2-flouro-2-deoxy-myo-inositol 1,4,5-triphosphate and scyllo-inositol 1,2,4-triphosphate, were synthesised in racemic form from suitably protected inositol precursors.
FLUORINATED ANALOGS OF INS(1,4,5)P3
Marecek, James F.,Prestwich, Glenn D.
, p. 5401 - 5404 (2007/10/02)
2-Fuoro-2-deoxy-Ins(1,4,5)P3 (2) and 2,2-difluoro-2-deoxy-Ins(1,4,5)P3 (3) were synthesized from protected inositol precursors.The monofluoro compound with free 3,6-hydroxyl groups underwent slow defluorination at pH > 13, as determi
The Allyl Group for Protection in Carbohydrate Chemistry. Part 20. Synthesis of 1L-1-O-Methyl-myo-inositol by Resolution of (+/-)-1,2,4-Tri-O-benzyl-myo-inositol
Gigg, Jill,Gigg, Roy,Payne, Sheila,Conant, Robert
, p. 1757 - 1762 (2007/10/02)
Racemic 1,2,4-tri-O-benzyl-myo-inositol was prepared by two new routes from (+/-)-1,4-di-O-benzyl-5,6-O-isopropylidine-myo-inositol, one route involving the crystalline intermediate (+/-)-1-O-allyl-3,6-di-O-benzyl-4,5-O-isopropylidine-myo-inositol.Oxidati
THE ALLYL GROUP FOR PROTECTION IN CARBOHYDRATE CHEMISTRY. PART 21. (+/-)-1,2:5,6- AND (+/-)-1,2:3,4-DI-O-ISOPROPYLIDENE-MYO-INOSITOL. THE UNUSUAL BEHAVIOUR OF CRYSTALS OF (+/-)-3,4-DI-O-ACETYL-1,2,5,6-TETRA-O-BENZYL-MYO-INOSITO ON HEATING AND COOLING: A '
Gigg, Jill,Gigg, Roy,Payne, Sheila,Conant, Robert
, p. 2411 - 2414 (2007/10/02)
Racemic 1,2-O-isopropylidene-myo-inositol was converted into a mixture of 1,2:5,6-, 1,2:3,4-, and 1,2:4,5-di-O-isopropylidene-myo-inositols which were resolved by g.l.c.The 1,2:4,5 and 1,2:5,6- isomers were isolated from the mixture as benzoate derivative
