142435-95-8

Basic information

• Product Name: 2,5-di-O-benzyl-1,6:3,4-di-O-isopropylidene-myo-inositol
• CAS NO: 142435-95-8
• Molecular Weight: 440.536
• Mol File: 142435-95-8.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 2,5-di-O-benzyl-1,6:3,4-di-O-isopropylidene-myo-inositol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-di-O-benzyl-1,6:3,4-di-O-isopropylidene-myo-inositol(142435-95-8)
• EPA Substance Registry System: 2,5-di-O-benzyl-1,6:3,4-di-O-isopropylidene-myo-inositol(142435-95-8)

Safety Data

• Hazardous Substances Data: 142435-95-8(Hazardous Substances Data)

Upstream product

• 142387-34-6 1,3,4,6-tetra-O-allyl-2,5-di-O-benzyl-myo-inositol 
• 136986-12-4 1,3,4,6-tetra-O-allyl-myo-inositol 
• 141040-66-6 2,5-di-O-phenylmethyl-myo-inositol 
• 77-76-9 2,2-dimethoxy-propane 
• 6404-82-6 (+/-)-1,2-O-isopropylidene-myo-inositol 
• 87-89-8 D-myo-inositol 
• 99756-37-3 (±)-3,6-di-O-benzoyl-1,2:4,5-di-O-isopropylidene-myo-inositol 
• 100-39-0 benzyl bromide 
• 51548-88-0 (+/-)-1,2:4,5-di-O-isopropylidene-myo-inositol 

Downstream Products

• 98906-25-3 (±)-1,2-O-isopropylidene-3,6-di-O-benzyl-myo-inositol 
• 111392-21-3 5,6-di-O-acetyl-1,2,3,4-tetra-O-benzyl-myo-inositol 
• 64656-21-9 5,6-di-O-allyl-1,2,3,4-tetra-O-benzyl-myo-inositol 
• 39698-23-2 1,2,3,4-tetra-O-benzyl-5-O-prop-1-enyl-myo-inositol 
• 39698-23-2 1,2,3,4-tetra-O-benzyl-6-O-prop-1-enyl-myo-inositol 
• 10583-42-3 6-O-allyl-1,2,3,4-tetra-O-benzyl-myo-inositol 
• 80971-00-2 (3aR,4S,5S,6R,7S,7aR)-4,5,7-Tris-benzyloxy-6-methoxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxole 
• 111446-91-4 (+/-)-1,2,4-tri-O-benzyl-5,6-O-isopropylidene-myo-inositol 
• 80971-02-4 (1S,2S,3R,4S,5S,6R)-3,4,6-Tris-benzyloxy-5-methoxy-cyclohexane-1,2-diol 
• 29847-13-0 (3aR,4S,5R,6S,7S,7aR)-4,5,6,7-Tetrakis-benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxole 
• 484-68-4 1-O-methyl-myo-inositol 
• 6195-66-0 rac-1,2,3,4-Tetra-O-benzyl-myo-inositol 
• 98906-27-5 (3aR,4R,5S,6S,7R,7aS)-4,7-Bis-benzyloxy-2,2-dimethyl-5,6-bis-(3-methyl-but-2-enyloxy)-hexahydro-benzo[1,3]dioxole 
• 98925-53-2 (1R,2S,3S,4R,5R,6S)-3,6-Bis-benzyloxy-4,5-bis-(3-methyl-but-2-enyloxy)-cyclohexane-1,2-diol 

Relevant articles and documents

Synthesis of the enantiomers of myo-inositol 1,2,4,5-tetrakisphosphate, a regioisomer of myo-inositol 1,3,4,5-tetrakisphosphate

Routes for the synthesis of racemic myo-inositol 1,2,4,5-tetrakisphosphate DL-Ins(1,2,4,5)P4 5ab and the chiral antipodes D- and L-myo-inositol 1,2,4,5-tetrakisphosphate 5a and 5b, respectively, are described. For the synthesis of racemate 5ab, 3,6-di-O-benzoyl-1,2:4,5-di-O-isopropylidene-myo-inositol 7ab is prepared in two steps from myo-inositol. The ketals are hydrolysed under acidic conditions to give DL-1,4-di-O-benzoyl-myo-inositol 8ab. Phosphitylation of compounds 8ab using chloro(diethoxy)-phosphine in the presence of base, followed by oxidation and a three-step deprotection strategy, gives DL-Ins(1,2,4,5)P4 5ab. The chiral tetrakisphosphates 5a and 5b are synthesized using a different route. The 4,5-isopropylidene group of DL-3,6-di-O-benzyl-1,2:4,5-di-O-isopropylidene-myo-inositol 13ab are selectively removed under mild acidic conditions to give diol 14ab. p-Methoxybenzylation at the 4,5-positions followed by acid hydrolysis of the cis-isopropylidene ketal affords cis-diol 16ab. Selective coupling of (S)-(+)-O-acetylmandelic acid with diol 16ab at the equatorial hydroxy group provides two diastereoisomers 18 and 19, which are separated by chromatography. Basic hydrolysis of the individual diastereoisomers provides the enantiomers 16a and 16b. Acidic hydrolysis gives D- and L-3,6-di-O-benzyl-myo-inositol 20a and 20b, respectively. Phosphitylation and oxidation of tetraols 20a and 20b gives the fully blocked derivatives, which are deprotected to give tetrakisphosphates 5a and 5b, respectively. The absolute configuration of compound 20a is established by a chemical method. DL-1,2:4,5-Di-O-isopropylidene-myo-inositol 12ab is coupled to (S)-(+)-O-acetylmandelic acid to give a mixture of bis-esters 26 and 27 and crystallisation of the mixture of diastereoisomers affords pure isomer 27. Basic hydrolysis gives the pure enantiomer 12a (for which the absolute configuration is known) and benzylation followed by acid hydrolysis gives tetraol 20a with the same physical properties as compound 20a prepared by a different route described previously. D-Ins(1,2,4,5)P4 5a is a potent mobiliser of intracellular Ca2+ ions in permeabilised platelets, while L-Ins(1,2,4,5)P4 5b is inactive.

The preparation and phosphorylation of 2,5- and 1D-2,6-di-O-benzyl-myo-inositol

1,3,4,6-Tetra-O-allyl-myo-inositol was converted into the 2,5-di-O-benzyl- and 2,5-di-O-p-methoxybenzyl ethers, and the products were deallylated to give the 2,5-di-O-benzyl (and p-methoxybenzyl) ethers of myo-inositol, which were converted into the mono-

The Allyl Group for Protection in Carbohydrate Chemistry. Part 18. Allyl and Benzyl Ethers of myo-Inositol. Intermediates for the Synthesis of myo-Inositol Triphosphates

Racemic 1,2:4,5-di-O-isopropylidene-myo-inositol was converted into racemic 1,2,4-tri-O-benzyl-myo-inositol, 1,2,4-tri-O-p-methoxybenzyl-myo-inositol and 2,4,5-tri-O-benzyl-myo-inositol using allyl groups for 'temporary' protection.The benzyl ethers are required as intermediates for the synthesis of the 'second messenger', inositol 1,4,5-triphosphate and its metabolite, inositol 1,3,4-triphosphate. 1,2,3,4-Tetra-O-benzyl-myo-inositol, and its two monoallyl and monoprop-1-enyl ethers, were also prepared as model compounds for phosphorylation studies of the vicinal 5,6-diol system which occurs in 1,2,4-tri-O-benzyl-myo-inositol.