866467-80-3

Upstream product

• 100-52-7 benzaldehyde 
• 367276-83-3 1,3-dibenzyl-2-oxo-5-(4-tert-butyldimethylsilyloxy-2-thiabut-3-enyl)-4-phenylthioimidazolidine 
• 367276-81-1 ({[(4S)-1,3-dibenzyl-2-oxo-5-(phenylthio)imidazolidin-4-yl]methyl}thio)acetaldehyde 
• 154097-01-5 (3aS,4S,6aR)-1,3-dibenzyl-2-oxohexahydro-1H-thieno[3,4-d]imidazole-4-carbaldehyde 
• 196930-46-8 (4R)-2-phenyl-1,3-thiazolidine-4-carboxylic acid 
• 866467-73-4 methyl ({[(4S)-1,3-dibenzyl-2-oxo-5-(phenylthio)-imidazolidin-4-yl]methyl}thio)acetate 
• 866467-75-6 (3aS,4S,6aR)-1,3-dibenzyl-4-(hydroxymethyl)tetrahydro-1H-thieno[3,4-d]imidazol-2(3H)-one 
• 866467-71-2 (3S,7aR)-6-benzyl-7-methoxy-3-phenyltetrahydro-5H-imidazo[1,5-c][1,3]thiazol-5-one 
• 112878-92-9 (3S,7aR)-6-benzyl-3-phenyldihydro-3H,5H-imidazo[1,5-c]thiazole-5,7(6H)-dione 
• 848302-22-7 (3S,7aR)-6-benzyl-7-hydroxy-3-phenyltetrahydro-5H-imidazo[1,5-c][1,3]thiazol-5-one 
• 866467-76-7 methyl 5-[(3aS,4S,6aR)-1,3-dibenzyl-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]-5-hydroxypentanoate 
• 124-63-0 methanesulfonyl chloride 
• 866467-74-5 (3aS,4S,6aR)-1,3-dibenzyl-4-({[tert-butyl(dimethyl)-silyl]oxy}methyl)tetrahydro-1H-thieno[3,4-d]imidazol-2(3H)-one 
• 866467-72-3 methyl ({[(4R)-1,3-dibenzyl-5-methoxy-2-oxo-imidazolidin-4-yl]methyl}thio)acetate 

Downstream Products

• 24459-54-9 N,N'-dibenzylbiotin methyl ester 
• 58-85-5 biotin 
• 112938-17-7 methyl (5Z)-5-[(3aS,6aR)-1,3-dibenzyl-2-oxohexahydro-4H-thieno[3,4-d]imidazol-4-ylidene]pentanoate 

Relevant academic research and scientific papers

An unusual stereochemical outcome of radical cyclization: Synthesis of (+)-biotin

An enantioselective synthesis of (+)-biotin 1 starting from naturally available cysteine is described. The key steps are the unusual stereochemical outcome of radical cyclization of compound 10 to prepare 5,5-fused system 11, and the introduction of C4-sidechain at C6 in 13 via a Grignard reaction.