117307-15-0

Upstream product

• 58706-20-0 (+/-)-3,6-di-O-benzyl-1,2:4,5-di-O-isopropylidene-myo-inositol 
• 35949-67-8 (±)-1,4-di-O-benzyl-myo-inositol 
• 77-76-9 2,2-dimethoxy-propane 
• 100-39-0 benzyl bromide 
• 6404-82-6 (+/-)-1,2-O-isopropylidene-myo-inositol 
• 87-89-8 D-myo-inositol 
• 141040-66-6 2,5-di-O-phenylmethyl-myo-inositol 
• 98906-25-3 (±)-1,2-O-isopropylidene-3,6-di-O-benzyl-myo-inositol 
• 141-78-6 ethyl acetate 
• 51548-88-0 (+/-)-1,2:4,5-di-O-isopropylidene-myo-inositol 
• 176200-07-0 (3aS,4S,4aR,7aR,8S,8aR)-4,8-Bis-benzyloxy-2,2,6,6-tetramethyl-hexahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxole 
• 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 
• 99756-37-3 (±)-3,6-di-O-benzoyl-1,2:4,5-di-O-isopropylidene-myo-inositol 

Downstream Products

• 146572-17-0 (+/-)-3,6-di-O-benzyl-4,5-di-O-butyryl-1,2-O-isopropylidene-myo-inositol 
• 127833-07-2 C₄₇H₅₀N₄O₈P₂ 
• 111446-91-4 (+/-)-3,4,6-tri-O-benzyl-1,2-O-isopropylidene-myo-inositol 
• 141986-98-3 Methyl-phosphinic acid (3aR,4S,5R,6R,7S,7aS)-4,7-bis-benzyloxy-2,2-dimethyl-6-methylphosphinoyloxy-hexahydro-benzo[1,3]dioxol-5-yl ester 
• 98906-26-4 (3aR,4R,5S,6S,7R,7aS)-5,6-Bis-allyloxy-4,7-bis-benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxole 
• 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 
• 117307-15-0 D-(+)-3,6-di-O-benzyl-1,2-O-isopropylidene-myo-inositol 
• 152697-30-8 1D-1,4-di-O-benzyl-2,3-O-isopropylidene-myo-inositol 

Relevant academic research and scientific papers

Facile selective cleavage of a myo-inositol trans-isopropylidene acetal in the presence of a cis-isopropylidene acetal

1,2:4,5-Di-O-isopropylidene myo-inositol acetals were selectively deprotected at the 4,5-trans position using Amberlite-120 (H+) resin in CHCl3/MeOH at room temperature over 24-48 h to afford the corresponding cis-1,2-O-isopropyliden

Kinetic resolution of (±)-1,2-O-isopropylidene-3,6-di-O-benzyl-myo- inositol by lipases: An experimental and theoretical study on the reaction of a key precursor of chiral inositols

The study on kinetic resolution of two myo-inositol derivatives by lipases is reported. Treatment of the triether derivative, (±)-1,2-O- isopropylidene-3,5,6-tri-O-benzyl-myo-inositol, with acylating agents in the presence of different lipases did not aff

Synthesis and in vitro anticancer activity evaluation of novel bioreversible phosphate inositol derivatives

The chemistry and biology of phosphorylated inositols have become intense areas of research during the last two decades due to their involvement in various cellular signaling processes. However, the metabolic instability by phosphatases or kinases and poo

Direct selective and controlled protection of multiple hydroxyl groups in polyols via iterative regeneration of stannylene acetals

A direct selective protection (O-benzylation) of two or more hydroxyl groups in polyols displaying diverse structural patterns was made possible by the establishment of conditions that enable an efficient turnover for the Bu2Sn group, initially

AKT INHIBITORS, PHARMACEUTICAL COMPOSITIONS, AND USES THEREOF

Disclosed are inhibitors of the serine/threonine kinase Akt, pharmaceutical compositions comprising such inhibitors, and a method of preventing or treating a disease or condition in an animal by the use of such inhibitors. The Akt inhibitors have the form

A more convenient and general procedure for O-monobenzylation of diols via Stannylenes: A critical reevaluation of the Bu2SnO method

A more consistent, straightforward, and economical protocol for generation of stannylene species and their reaction with BnBr leading to products of O-monobenzylation of diols has been set. It has shown to be specially indicated for substrates bearing vicinal trans 1,2-diol moieties on cyclohexane backbones, which are more resistant to these transformations. Such protocol has been successfully applied to myo-inositol derivatives and acyclic diols.

Selective Deprotection of Acetals with Me3SiCH2MgCl. Peterson-Type Olefination of Acetals

By employing the chelation strategy, treatment of an acetal of a contiguous diol with Me3SiCH2-MgCl liberates the corresponding diol regioselectively. In addition, acetals of different structural variety are transformed upon treatment with Me3SiCH2MgCl and ZnI2 into the corresponding olefination products in good yield.

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.

Selective deprotection of an acetal group in monosaccharide derivatives and related compounds using Me3SiCH2MgCl

Treatment of an acetal of a contiguous diol with Me3SiCH2MgCl liberates the corresponding diol regioselectively; chelation is used to rationalize the selectivity.

Cyclic carbonates as protecting groups in cyclitol chemistry

Keywords: Cyclic carbonates; Protecting group; ethylene carbonate; Inositol derivatives; myo-Inositol 1,2-carbonate