112938-17-7

Upstream product

• 866467-80-3 5-((3aR,6S,6aS)-1,3-Dibenzyl-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-5-methanesulfonyloxy-pentanoic acid methyl ester 
• 196930-46-8 (4R)-2-phenyl-1,3-thiazolidine-4-carboxylic acid 
• 112878-96-3 6-[(3S,7R,7aR)-6-benzyl-5-oxo-3-phenyltetrahydro-1H-imidazo[1,5-c][1,3]thiazol-7-yl]-6-oxohexanoic acid 
• 848302-18-1 (3S,7R,7aR)-6-benzyl-7-(1-hydroxy-2-oxocyclohexyl)-3-phenyl-tetrahydro-5H-imidazo[1,5-c][1,3]thiazol-5-one 
• 848302-22-7 (3S,7aR)-6-benzyl-7-hydroxy-3-phenyltetrahydro-5H-imidazo[1,5-c][1,3]thiazol-5-one 
• 848302-21-6 methyl 6-[(3S,7R,7aR)-6-benzyl-5-oxo-3-phenyltetrahydro-5H-imidazo[1,5-c][1,3]thiazol-7-yl]-6-oxohexanoate 
• 67-56-1 methanol 
• 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 
• 100-52-7 benzaldehyde 
• 866467-76-7 methyl 5-[(3aS,4S,6aR)-1,3-dibenzyl-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]-5-hydroxypentanoate 
• 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 
• 866467-73-4 methyl ({[(4S)-1,3-dibenzyl-2-oxo-5-(phenylthio)-imidazolidin-4-yl]methyl}thio)acetate 

Downstream Products

• 58-85-5 biotin 
• 24459-54-9 N,N'-dibenzylbiotin methyl ester 

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.

Diastereoselective amidoalkylation of (3S,7aR)-6-benzyl-7-hydroxy-3- phenyltetrahydro-5H-imidazo[1,5-c][1,3]thiazol-5-one: A short and highly efficient synthesis of (+)-biotin

(Chemical Equation Presented) A short and highly efficient synthesis of (+)-biotin in 10 steps with 20% overall yield has been achieved from L-cysteine involving amidoalkylation of hydroxy imidazothiazolone 4 via an acyliminium ion intermediate to furnish C-7-substituted imidazothiazolones 5b as the key step.