181783-28-8

Basic information

• Product Name: (1S,2S,3R,4S,5R,6R)-5-Allyloxy-3,6-bis-benzyloxy-cyclohexane-1,2,4-triol
• CAS NO: 181783-28-8
• Molecular Weight: 400.472
• Mol File: 181783-28-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (1S,2S,3R,4S,5R,6R)-5-Allyloxy-3,6-bis-benzyloxy-cyclohexane-1,2,4-triol(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S,3R,4S,5R,6R)-5-Allyloxy-3,6-bis-benzyloxy-cyclohexane-1,2,4-triol(181783-28-8)
• EPA Substance Registry System: (1S,2S,3R,4S,5R,6R)-5-Allyloxy-3,6-bis-benzyloxy-cyclohexane-1,2,4-triol(181783-28-8)

Safety Data

• Hazardous Substances Data: 181783-28-8(Hazardous Substances Data)

Upstream product

• 181525-55-3 (1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (3aR,4R,5R,6S,7S,7aR)-6-allyloxy-4,7-bis-benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-5-yl ester 
• 114218-23-4 (+/-)-1-O-allyl-2,5-di-O-benzyl-3,4-O-isopropylidene-scyllo-inositol 
• 114218-23-4 (+/-)-1-O-allyl-3,6-di-O-benzyl-4,5-O-isopropylidene-myo-inositol 

Relevant 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

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.