23262-92-2

Upstream product

• 26276-99-3 rac-1,4,5,6-tetra-O-benzyl-myo-inositol 
• 65-85-0 benzoic acid 
• 87-89-8 D-myo-inositol 
• 29847-13-0 (±)-1,4,5,6-tetra-O-benzyl-2,3-O-isopropylidene-myo-inositol 
• 6404-82-6 (+/-)-1,2-O-isopropylidene-myo-inositol 
• 98-88-4 benzoyl chloride 
• 6691-27-6 (+/-)-cis-1,2-O-cyclohexylidene-3,4,5,6-tetrakis-O-benzyl myo-inositol 

Downstream Products

• 261621-51-6 1‐O‐benzoyl‐scyllo‐inositol 
• 260560-25-6 1,3,5-tri-O-benzoyl-scyllo-inositol 
• 261617-70-3 1,2,3-tri-O-benzoyl-scyllo-inositol 4,5,6-tris(diethyl phosphonate) 
• 260560-26-7 DL-1,3,5-tri-O-benzoyl-scyllo-inositol 2,4,6-tris(diethyl phosphonate) 
• 261617-72-5 1,4-di-O-benzoyl-scyllo-inositol 2,3,5,6-tetrakis(diethyl phosphite) 
• 62700-84-9 DL-1-O-benzoyl-3,4,5,6-tetra-O-benzylmyoinosose-2 
• 85716-58-1 DL-2-O-Benzoyl-3,4,5,6-tetra-O-benzyl-1-deoxy-1-fluoro-scyllo-inositol 
• 129707-22-8 (-)-1D-3,4,5,6-Tetra-O-benzyl-1-deoxy-1-fluoro-myo-inositol 
• 120444-23-7 (+)-1L-3,4,5,6-Tetra-O-benzyl-1-deoxy-1-fluoro-myo-inositol 
• 120444-22-6 (1S,2S,3R,4S,5R,6R)-2,3,4,5-Tetrakis-benzyloxy-6-fluoro-cyclohexanol 
• 120444-20-4 (1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (1S,2R,3S,4S,5R,6S)-2,3,4,5-tetrakis-benzyloxy-6-fluoro-cyclohexyl ester 
• 120401-18-5 (1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (1R,2S,3R,4R,5S,6R)-2,3,4,5-tetrakis-benzyloxy-6-fluoro-cyclohexyl ester 
• 120444-21-5 (1R,2R,3S,4R,5S,6S)-2,3,4,5-Tetrakis-benzyloxy-6-fluoro-cyclohexanol 

Relevant academic research and scientific papers

Efficient regioselective protection of myo-inositol via facile protecting group migration

A cis-1,2-cyclohexanediol, 1,4,5,6-tetra-O-benzyl-myo-inositol, was selectively protected at the axial C2-hydroxyl via acid-mediated rearrangement of the corresponding 1,2-orthoacetate, or via the base-induced migration of a protecting group that had previously been easily installed with complete regioselectivity at the adjacent equatorial hydroxyl. Esters 4a-6a were synthesized in high yields (75-82%) while sulfonate 7a and silyl ether 8a were obtained in 85 and 31% yields, respectively. The migration of the esters induced by DBU results in equilibrium between regioisomers favouring the C2 protected isomer, but NaH induced migration of sulfonyl and silyl groups results in complete migration from equatorial to axial hydroxyl groups.

INOSITOL-BASED MOLECULAR TRANSPORTERS AND PROCESSES FOR THE PREPARATION THEREOF

Inositol derivatives in accordance with the present invention are effective in significantly enhancing the transportation of various therapeutic molecules across a biological membrane, which may include the plasma membrane, nuclear membrane or blood-brain barrier.

Synthesis of all possible regioisomers of scyllo-inositol phosphate

scyllo-Inositol is the all equatorial stereoisomer of myo-inositol. All possible 12 regioisomers of scyllo-inositol phosphate were synthesized for the first time via a scyllo-inositol benzoate intermediate, which was derived from a myo-inositol derivative. The stereoinversion of myo-inositol into scyllo-inositol was accomplished by Mitsunobu reaction of the vicinal cis- diol. The requisite intermediates, scyllo-inositol benzoates were obtained by benzoyl migration or random benzoylation, and phosphorylated to give scyllo- IP(n). (C) 1999 Elsevier Science Ltd.

Synthesis of 3,4,5,6-tetrakisphosphates of DL-1,2-dideoxy-1,2-difluoro-myo-inositol and DL-1,2-dideoxy-1,2-difluoro-scyllo-inositol as analogues of DL-myo-inositol 3,4,5,6-tetrakisphosphate

DL-1,2-Dideoxy-1,2-difluoro-myo-inositol was prepared from DL-3,4,5,6-tetra-O-benzyl-myo-inositol in five steps in an overall yield of 36%. The fluoro substituents were introduced with DAST in separate steps by displacement of hydroxy substituents with inversion of stereochemistry. Difluorination could not be achieved in one step because of competing formation of a 1,4-anhydro derivative. DL-1,2-Dideoxy-1,2-difluoro-scyllo-inositol was prepared in 42% overall yield using similar chemistry, with the required inversion of one stereocentre being accomplished by displacement of a tosyl group with caesium propionate. Both difluoroinositol analogues increased the levels of phytic acid (InsP6) in a skeletal muscle cell line. Each compound was tetraphosphorylated with dibenzyl N,N-diisopropylphosphoramidite in the presence of 1H-tetrazole, with subsequent oxidation of the phosphite with MCPBA. The P-OBn groups were removed by H2/Pd-C, and the sodium salts of the tetrakisphosphates of the difluoroinositol analogues were obtained by cation exchange.

Mechanism and inhibition of inositol monophosphatase

The design and synthesis of inhibitors of inositol monophosphatase (IMPase, B.C. 3.1.3.25) based on natural substrates and lead compounds discovered by screening is discussed. The physiologically relevant form of the enzyme and a likely mechanism have been deduced from structure-activity relationships, site-directed mutagenesis experiments, X-ray crystallography and molecular modelling.

Synthesis of 2- and 6-Deoxyinostol 1-Phosphate and the Role of the Adjecent Hydroxy Groups in the Mechanism of Inositol Monophosphatase

The 2- and 6-hydroxy groups of myo-inositol 1-phosphate have been shown to be independently associated with the mechanisms of hydrolysis and binding in the dephosporylation of the substrate by inositol monophosphatase.

A Synthesis of (-)-1L-1-Deoxy-1-fluoro-myo-inositol; a Compound of Potential Use in sorting out the Phosphatidylinositol Response

A synthesis of 1L-1-deoxy-1-fluoro-myo-inositol in optically pure form starting from myo-inositol is reported.