253336-68-4

Upstream product

• 5447-02-9 3,4-dibenzyloxybenzaldehyde 
• 16047-57-7 (((4-bromo-1,2-phenylene)bis(oxy))bis(methylene))dibenzene 
• 17345-61-8 3,4-dihydroxybenzonitrile 
• 100-44-7 benzyl chloride 

Downstream Products

• 5447-02-9 3,4-dibenzyloxybenzaldehyde 
• 20728-73-8 5,7,3',4'-tetra-O-benzyl-(+)-catechin 
• 203571-40-8 3-(3,4-bis-benzyloxy-phenyl)-acrylic acid ethyl ester 
• 87292-49-7 5,7,3',4'-tetra-O-benzylepicatechin 
• 87292-54-4 (+)-(2R)-5,7-bis(benzyloxy)-2-[3,4-bis(benzyloxy)phenyl]chroman-3-one 
• 362632-29-9 (E)-3-(3,4-bis(benzyloxy)phenyl)prop-2-en-1-ol 
• 664351-39-7 (2R,3R,4S)-5,7,3',4'-tetrabenzyloxy-4-(2''-ethoxyethoxy)flavan-3-ol 
• 732298-08-7 (E)-3-[2,4-bis(benzyloxy)-6-hydroxyphenyl]-1-[3,4-bis(benzyloxy)phenyl]propene 
• 732298-11-2 (+)-(1S,2S)-3-[2,4-bis(benzyloxy)-6-hydroxyphenyl]-1-[3,4-bis(benzyloxy)phenyl]propane-1,2-diol 
• 918157-97-8 (E)-3-[2,4-bis(benzyloxy)-6-(tert-butyldimethylsilyloxy)phenyl]-1-[3,4-bis(benzyloxy)phenyl]propene 
• 918158-03-9 (1S,2S)-3-[2,4-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-phenyl]-1-(3,4-bis-benzyloxy-phenyl)-propane-1,2-diol 
• 1274238-83-3 5-[3,4-bis(phenylmethoxy)phenyl]-tetrazole 

Relevant academic research and scientific papers

Utility of Nitrogen Extrusion of Azido Complexes for the Synthesis of Nitriles, Benzoxazoles, and Benzisoxazoles

The utility of the nitrogen extrusion reaction of azido complexes, generated in situ from the corresponding aldehydes or ketones with TMSN3 in the presence of ZrCl4 or TfOH, has been described. These azido complexes could undergo three different pathways, depending on the substrates. First, azido methanolate complexes or imine diazonium ions could lead to benzisoxazole products via an intramolecular nucleophilic substitution. Second, imine diazonium ions could also undergo either the elimination of proton to provide nitrile products in good to excellent yields or an aryl migration, followed by an intramolecular nucleophilic addition, to give benzoxazole products in good yields.

A new spirobifluorene-bridged bipolar system for a nitric oxide turn-on fluorescent probe

Chemical equations presented. A new spirobifluorene-bridged bipolar molecule (EDADO) as a nitric oxide (NO) turn-on fluorescent probe was designed and synthesized. The fluorescence of EDADO is strongly quenched by photoinduced electron transfer (PET) from the electron-donating o-phenylenediamine-containing biphenyl branch to the orthogonally arranged electron-accepting 1,3,4-oxadiazole-containing conjugated oligoaryl system. Upon reacting with NO, EDADO is converted to EDADO-T, which exhibits strong fluorescence due to the suppression of PET.

Total synthesis of 14C-labeled procyanidin B2

During the last decades, many in vitro and in vivo studies have shown the beneficial effects on health of procyanidins. However, their absorption and metabolism is still not fully understood and some aspects are still controversial. In order to have a clearer picture of the metabolism of procyanidins, the use of labelled compounds is essential. In this context, the enantioselective synthesis of 14C-radiolabelled procyanidin B2 was developed in our laboratories. It was achieved in fourteen 'hot' steps, involving as key steps the Sharpless dihydroxylation of an elaborated alkene, a stereoselective intramolecular cyclization to benzylated (+)-catechin and the condensation of two (-)-epicatechin units. 11 mCi of protected procyanidin B2 were obtained from 524 mCi of potassium [14C]cyanide. Copyright

First total synthesis of14C-labeled procyanidin B2 - A milestone toward understanding cocoa polyphenol metabolism

The idea that foods consumed for pure pleasure could provide health benefits received much recognition in the recent years. Among these foods, cocoa and dark chocolate are particularly rich in procyanidins, one of the major dietary families of polyphenols. We developed the first asymmetric total synthesis of procyanidin B2 and applied it to the preparation of a regioselectively radiolabeled 14C-analogue, which will be used to strengthen our knowledge on the metabolism of procyanidins. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

A simple and highly efficient one-pot chemoselective synthesis of nitriles from aldehydes: Mechanistic insight and selectivity control through modulation of electronic and steric factors

Aldehydes are converted into nitriles in a one-pot reaction by treatment with H2NOH·HCl in dipolar aprotic solvents under heating. Amongst various solvents NMP offers the best results. No competitive ether cleavage (e.g. methoxy, benzyloxy) or aromatic nucleophilic substitution (e.g. nitro or chloro) takes place for substrates beating such functionalities. Electronic and steric factors around the aldehyde carbon affect the rate of nitrile formation. Excellent to moderate selectivity is observed during intermolecular competition between pair of aldehydes with varying electronic and steric requirements.

One-pot synthesis of nitriles from aldehydes under microwave irradiation: Influence of the medium and mode of microwave irradiation on product formation

Chemoselective transformation of aldehyde to nitrile takes place in a one-pot reaction by treatment with H2NOHHCl in N- methyl-2-pyrrolidinone (NMP) under microwave irradiation using convection mode.