1041862-06-9

Upstream product

• 109976-46-7 (5-ethoxy-5-oxopentyl)zinc(II) iodide 
• 28092-52-6 (3aS,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2,4-dione 
• 14660-52-7 ethyl 5-bromovalerate 
• 2067-33-6 5-bromopentanoic acid 

Downstream Products

• 292151-18-9 ethyl (3aS,4Z,6aR)-5-[1,3-dibenzyl-2,3,3a,4,6,6a-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-5-ylidene]-pentanoate 
• 292151-19-0 (3aS,4S,6aR)-5-(1,3-dibenzyl-2,3,3a,4,6,6a-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-5-ylidene)pentanoic acid ethyl ester 
• 58-85-5 biotin 

Relevant academic research and scientific papers

Synthetic studies on (+)-biotin, Part 11:[1] Application of Cinchona alkaloid-mediated asymmetric alcoholysis of meso-cyclic anhydride in the total synthesis of (+)-biotin

A practical and asymmetric process for the totalsyn thesis of (+)-biotin (1) has been accomplished starting from cis-1,3-dibenzyl-2-oxoimidazolidine-4,5- dicarboxylic acid (2). This approach features a highly enantioselective alcoholysis of mesocyclic anhydride 3 into (4S,5R)-cinnamylhemiest er 4 mediated by Cinchona alkaloids. Another attractive feature of this synthesis involves the use of recyclable palladium nanoparticles-catalyzed assembly of the 4-carboxybutyl chain at C-4 in (3aS,6aR)-thiolactone 7 employing an improved Fukuyamatype cross-coupling reaction.

Facile synthesis of (+)-biotin via Fukuyama coupling reaction

Treatment of a thiolactone 2 with a zinc reagent 3 in the presence of PdCl2(PPh3)2 (10 mol%) allowed installation of a C-2 side chain of (+)- biotin in a highly efficient manner, which enabled synthesis of (+)biotin in three steps from 2. (C) 2000 Elsevier Science Ltd.

PROCESS FOR THE MANUFACTURE OF (+)-BIOTIN

Disclosed are processes for preparing synthetic biotin intermediates and a process for preparing biotin using said intermediates. In particular, disclosed is a process for the stereoselective total synthesis of the natural product (+)-biotin of formula (I).