151526-80-6

Basic information

• Product Name: <3aS-(3aα,4Z,6aα)>-5-imidazol-4-ylidene>pentanoic acid methyl ester
• Synonyms: <3aS-(3aα,4Z,6aα)>-5-imidazol-4-ylidene>pentanoic acid methyl ester
• CAS NO: 151526-80-6
• Molecular Weight: 346.45
• Mol File: 151526-80-6.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: <3aS-(3aα,4Z,6aα)>-5-imidazol-4-ylidene>pentanoic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: <3aS-(3aα,4Z,6aα)>-5-imidazol-4-ylidene>pentanoic acid methyl ester(151526-80-6)
• EPA Substance Registry System: <3aS-(3aα,4Z,6aα)>-5-imidazol-4-ylidene>pentanoic acid methyl ester(151526-80-6)

Safety Data

• Hazardous Substances Data: 151526-80-6(Hazardous Substances Data)

Upstream product

• 151415-06-4 Δ^2,3,N-(Phenylmethyl)-2-(carbomethoxybutyl)dihydrothiophene-4(S)-carbamoyl azide 
• 151415-05-3 N-(Phenylmethyl)-3(R)-bromo-2(R)-(carbomethoxybutyl)tetrahydrothiophene-4(S)-carbamoyl azide 
• 1026976-17-9 C₁₈H₂₃BrClNO₃S 
• 161458-88-4 5-((2R,3R,4S)-3-Bromo-4-{[1-phenyl-meth-(E)-ylidene]-amino}-tetrahydro-thiophen-2-yl)-pentanoic acid methyl ester 
• 161458-89-5 <2S-(2α,3β,4α)>-3-Bromotetrahydro-4-<(phenylmethyl)amino>-2-thiophenepentanoic acid methyl ester 
• 100-52-7 benzaldehyde 
• 449729-44-6 (S)-7-[(2R,4R)-3-(tert-butoxycarbonyl)-2-phenylthiazolidin-4-yl]-7-methoxycarbonyloxy-6-oxoheptanoic acid methyl ester 
• 449729-42-4 (S)-7-[(2R,4R)-3-(tert-butoxycarbonyl)-2-phenylthiazolidin-4-yl]-7-hydroxy-6-oxoheptanoic acid methyl ester 

Downstream Products

• 76335-62-1 5-[(3aS)-1( oder !3)-benzyl-2-oxo-(3ar,6ac)-hexahydro-thieno[3,4-d]imidazol-4t-yl]-valeric acid 
• 452100-87-7 (3aS,4Z,6aR)-5-{hexahydro-1,3-dibenzyl-2-oxo-4H-thieno[3,4-d]imidazol-4-ylidene}pentanoic acid 
• 58-85-5 biotin 
• 452100-86-6 (3aS,4Z,6aR)-5-{hexahydro-1,3-dibenzyl-2-oxo-4H-thieno[3,4-d]imidazol-4-ylidene}pentanoic acid methyl ester 
• 151526-81-7 <3aS-(3aα,4β,6aα)>-Hexahydro-2-oxo-1-(phenylmethyl)-1H-thieno<3,4-d>imidazole-4-pentanoic acid methyl ester 

Relevant articles and documents

A novel synthesis of (+)-biotin from L-cysteine

(+)-Biotin (1) was synthesized in 25% overall yield over 11 steps from L-cysteine. The contiguous asymmetric centers at C-3a and C-6a were formed through a novel and highly stereoselective Lewis base-catalyzed cyanosilylation of α-amino aldehyde 3 to provide anti- O-TMS-cyanohydrin 4 with high stereoselectivity and in high yield (anti/syn = 92:8, 96%). Treatment of 4 with a di-Grignard reagent, 1,4-bis(bromomagnesio)butane, followed by carbon dioxide, efficiently installed the 4-carboxybutyl chain at C-4 to give keto acid 5. The final cyclization to bicyclic compound 7b, a precursor to 1, was realized by a palladium-catalyzed intramolecular allylic amination of cis-allylic carbonate 6b that was elaborated from 5.