154097-01-5

Upstream product

• 555-16-8 4-nitrobenzaldehdye 
• 367276-83-3 1,3-dibenzyl-2-oxo-5-(4-tert-butyldimethylsilyloxy-2-thiabut-3-enyl)-4-phenylthioimidazolidine 
• 866467-75-6 (3aS,4S,6aR)-1,3-dibenzyl-4-(hydroxymethyl)tetrahydro-1H-thieno[3,4-d]imidazol-2(3H)-one 
• 848302-22-7 (3S,7aR)-6-benzyl-7-hydroxy-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 
• 866467-71-2 (3S,7aR)-6-benzyl-7-methoxy-3-phenyltetrahydro-5H-imidazo[1,5-c][1,3]thiazol-5-one 
• 866467-72-3 methyl ({[(4R)-1,3-dibenzyl-5-methoxy-2-oxo-imidazolidin-4-yl]methyl}thio)acetate 
• 83889-77-4 (4S,5R)-1,3-bisbenzyl-2-oxo-5-(methoxycarbonyl)imidazolidin-4-carboxylic acid 
• 153991-79-8 ((R)-1,3-Dibenzyl-2,5-dioxo-imidazolidin-4-ylmethylsulfanyl)-acetic acid methyl ester 
• 367276-80-0 (R)-1,3-Dibenzyl-5-hydroxy-hexahydro-4-oxa-7-thia-1,3-diaza-azulen-2-one 
• 51591-75-4 cis-1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid 
• 56198-73-3 dimethyl cis-1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylate 
• 28092-62-8 (3aS,6aR)-1,3-dibenzyltetrahydro-1H-furo[3,4-d]imidazole-2,4-dione 
• 367276-81-1 ({[(4S)-1,3-dibenzyl-2-oxo-5-(phenylthio)imidazolidin-4-yl]methyl}thio)acetaldehyde 

Downstream Products

• 367276-82-2 (3aS,4R,6aR)-1,3-dibenzyl-4-[(1E,3E)-4-methoxycarbonyl-1,3-butanedienyl]-1H-tetrahydrothieno[3,4-d]imidazol-2(3H)-one 
• 33607-60-2 (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 
• 153991-84-5 (E)-5-[(3aR,6aS)-1,3-Dibenzyl-2-oxo-hexahydro-thieno[3,4-d]imidazol-(6E)-ylidene]-pent-3-enoic acid 
• 24459-54-9 N,N'-dibenzylbiotin methyl ester 
• 58-85-5 biotin 
• 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 
• 866467-76-7 methyl 5-[(3aS,4S,6aR)-1,3-dibenzyl-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]-5-hydroxypentanoate 
• 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.

Synthetic studies on d-biotin, part 8: An efficient chemoenzymatic approach to the asymmetric total synthesis of d-biotin via a polymer-supported PLE-mediated desymmetrization of meso-symmetic dicarboxylic esters

A practical chemoenzymatic method for the asymmetric total synthesis of d-biotin (1) starting from the commercially available cis-1,3-dibenzyl-2- imidazolidone-4,5-dicarboxylic acid (2) has been developed. The key step of the synthesis is the highly enantioselective hydrolysis of meso-dicarboxylic esters by a polymer-supported pig liver esterase and introduction of a formyl group at the C-4 position in 4 via a Grignard reaction. The polymer-supported PLE can be recovered quantitatively from the reaction mixture by simple filtration and reused without significant loss of activity.

Total synthesis of D-(+)-biotin

The total synthesis of D-(+)-biotin has been described starting from D-(+)-glucosamine using acyliminium chemisty. A total synthesis of D-(+)-biotin is described starting from D-(+)-glucosamine using acyliminium chemistry.