213122-44-2

Upstream product

• 2930-05-4 Benzyloxymethyl-oxiran 
• 105-13-5 4-Methoxybenzyl alcohol 
• 100-51-6 benzyl alcohol 
• 824-94-2 p-methoxybenzyl chloride 
• 108836-41-5 2-((4-methoxybenzyloxy)methyl)oxirane 
• 162427-33-0 1-benzyloxy-3-(p-methoxybenzyloxy)propan-2-ol 

Downstream Products

• 1201901-80-5 (+/-)-2-benzyloxymethyl-2-(4-methoxybenzyloxymethyl)oxirane 
• 1253120-56-7 C₂₃H₃₀O₄Si 
• 367263-52-3 Tetradecyl 5-[(benzyloxy)methyl]-5-[(4-methoxyphenoxy)methyl]tetrahydro-2-furancarboxylate 
• 367263-50-1 Methyl 5-[(benzyloxy)methyl]-5-[(4-methoxyphenoxy)methyl]tetrahydro-2-furancarboxylate 
• 367263-49-8 5-benzyloxymethyl-5-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2-carboxylic acid 
• 367263-47-6 5-[(Benzyloxy)methyl]-5-[(4-methoxyphenoxy)methyl]tetrahydro-2-furancarbonitrile 
• 367263-43-2 5-[(Benzyloxy)methyl]-5-[(4-metoxyphenoxy)methyl]tetrahydro-2-furanol 
• 367263-45-4 2-benzyloxymethyl-5-chloro-2-(4-methoxy-benzyloxymethyl)-tetrahydro-furan 

Relevant academic research and scientific papers

The scope and limitation of the regio- and enantioselective hydrolysis of aliphatic epoxides using Bacillus subtilis epoxide hydrolase, and exploration toward chirally differentiated tris(hydroxymethyl)methanol

The substrate specificity of an engineered Bacillus subtilis epoxide hydrolase, which so far had shown high activity and enantioselectivity with 1-benzyloxymethyl-1-methyloxirane, has been studied by altering the methyl substituent into hydrogen, oxygen-containing functionalities, and unsaturated homologs. High enantioselectivity (E = 44) was observed with 1-benzyloxymethyl-1-vinyloxirane with a proper catalytic activity. The elaboration of the reaction conditions and work-up procedures enabled a preparative-scale kinetic resolution, to give (R)-2-benzyloxymethyl-3-butene-1, 2-diol and its antipodal (R)-epoxide in high ees.

Synthesis of 2,5-dihydrofurans via alkylidene carbene insertion reactions

The insertion reaction of alkylidene carbenes is demonstrated to be an effective method for the synthesis of 2,5-dihydrofuran ring systems. The best results have been obtained on substrates containing electron-withdrawing substituents, which appear less prone to the competing rearrangement reaction. This insight has led to the development of a new method for the synthesis of the core structure of the squalestatin-zaragozic acid natural products.

5-Acyloxy-5-hydroxymethyltetrahydro-2-furancarboxylate as a novel template for protein kinase C (PKC) binding

A series of alkyl tetrahydrofuran-2-carboxylates (1-4) bearing a new set of three pharmacophoric groups were tested as protein kinase C (PKC) ligands. The compounds were synthesized from commercially available glycidyl 4-methoxyphenyl ether. The correlation between their binding affinities for PKC-α and a conformational fit to phorbol ester indicates they mimic a pharmacophore model comprising the C20-OH, C3-C=O and C9-OH rather than that including the C13-C=O moiety.

Conformationally constrained analogues of diacylglycerol (DAG). 14.1 Dissection of the roles of the sn-1 and sn-2 carbonyls in DAG mimetics by isopharmacophore replacement

The replacement of the sn-1 and sn-2 carbonyl esters in DAG-surrogate lactones by sulfonate esters showed that their isosteric properties in protein kinase C binding are controlled by the location of the hydrophobic alkyl chain on the molecule. The CO and SO2 groups appear to be true isosteres only when they are adjacent to the alkyl chain, which is presumed to insert normal to the lipid bilayer.