5785-98-8

Upstream product

• 16047-57-7 (((4-bromo-1,2-phenylene)bis(oxy))bis(methylene))dibenzene 

Downstream Products

• 5736-83-4 3,4-bis(benzyloxy)[CO-14C]benzaldehyde 
• 1126481-96-6 C₂₄⁽¹⁴⁾CH₂₄O₄ 
• 1126481-74-0 (E)-3-[3,4-bis(benzyloxy)phenyl][3-14C]prop-2-en-1-ol 
• 1126481-75-1 (E)-3-[2,4-bis(benzyloxy)-6-(tert-butyldimethylsilyloxy)phenyl]-1-[3,4-bis(benzyloxy)phenyl][1-14C]propene 
• 1126481-78-4 C₄₈⁽¹⁴⁾CH₅₄O₇Si 
• 1126481-81-9 5,7,3',4'-tetra-O-benzyl[2-14C]catechin 
• 1126481-97-7 (2R)-5,6,3',4'-tetrakis(benzyloxy)[2-14C]flavan-3-one 
• 1126481-82-0 5,7,3',4'-tetra-O-benzyl[2-14C]epicatechin 

Relevant academic research and scientific papers

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.