367276-82-2

Basic information

• Product Name: (3aS,4R,6aR)-1,3-dibenzyl-4-[(1E,3E)-4-methoxycarbonyl-1,3-butanedienyl]-1H-tetrahydrothieno[3,4-d]imidazol-2(3H)-one
• Synonyms: (3aS,4R,6aR)-1,3-dibenzyl-4-[(1E,3E)-4-methoxycarbonyl-1,3-butanedienyl]-1H-tetrahydrothieno[3,4-d]imidazol-2(3H)-one
• CAS NO: 367276-82-2
• Molecular Weight: 434.559
• Mol File: 367276-82-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (3aS,4R,6aR)-1,3-dibenzyl-4-[(1E,3E)-4-methoxycarbonyl-1,3-butanedienyl]-1H-tetrahydrothieno[3,4-d]imidazol-2(3H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3aS,4R,6aR)-1,3-dibenzyl-4-[(1E,3E)-4-methoxycarbonyl-1,3-butanedienyl]-1H-tetrahydrothieno[3,4-d]imidazol-2(3H)-one(367276-82-2)
• EPA Substance Registry System: (3aS,4R,6aR)-1,3-dibenzyl-4-[(1E,3E)-4-methoxycarbonyl-1,3-butanedienyl]-1H-tetrahydrothieno[3,4-d]imidazol-2(3H)-one(367276-82-2)

Safety Data

• Hazardous Substances Data: 367276-82-2(Hazardous Substances Data)

Upstream product

• 65866-00-4 (E)-3-methoxycarbonyl-2-propenylidenetriphenylphosphorane 
• 154097-01-5 (3aS,4S,6aR)-1,3-dibenzyl-2-oxohexahydro-1H-thieno[3,4-d]imidazole-4-carbaldehyde 
• 24676-98-0 diethyl 3-methoxycarbonyl-2-propenylidenephosphonate 
• 83889-77-4 (4S,5R)-1,3-bisbenzyl-2-oxo-5-(methoxycarbonyl)imidazolidin-4-carboxylic acid 
• 51591-75-4 cis-1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid 
• 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 
• 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 
• 555-16-8 4-nitrobenzaldehdye 
• 780767-58-0 Acetic acid (R)-3-benzyloxy-3-((4S,5S)-1,3-dibenzyl-5-cyano-2-oxo-imidazolidin-4-yl)-2-oxo-propyl ester 
• 780767-55-7 (3aS,5S,6R,6aR)-1,3-Dibenzyl-6-benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hexahydro-furo[2,3-d]imidazol-2-one 
• 780767-59-1 (4S,5S)-1,3-Dibenzyl-5-((R)-1-benzyloxy-2,3-dihydroxy-propyl)-2-oxo-imidazolidine-4-carboxylic acid methyl ester 
• 780767-56-8 (3aS,5R,6R,6aR)-1,3-Dibenzyl-6-benzyloxy-5-((R)-1,2-dihydroxy-ethyl)-hexahydro-furo[2,3-d]imidazol-2-one 

Downstream Products

• 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 
• 58-85-5 biotin 
• 153991-84-5 (E)-5-[(3aR,6aS)-1,3-Dibenzyl-2-oxo-hexahydro-thieno[3,4-d]imidazol-(6E)-ylidene]-pent-3-enoic acid 

Relevant articles and documents

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.

A switch of reactivity profile in ionic intramolecular annulation reactions: A short and efficient synthesis of D-(+)-biotin

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