794518-65-3

Basic information

• Product Name: (2E,4S)-4-[N-benzyl-N-[(2E)-(4-chloro-3-methyl-2-butenyl)]amino]-5-(tert-butyldimethylsilyloxy)-2-penten-1-ol
• Synonyms: (2E,4S)-4-[N-benzyl-N-[(2E)-(4-chloro-3-methyl-2-butenyl)]amino]-5-(tert-butyldimethylsilyloxy)-2-penten-1-ol
• CAS NO: 794518-65-3
• Molecular Weight: 424.099
• Mol File: 794518-65-3.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (2E,4S)-4-[N-benzyl-N-[(2E)-(4-chloro-3-methyl-2-butenyl)]amino]-5-(tert-butyldimethylsilyloxy)-2-penten-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (2E,4S)-4-[N-benzyl-N-[(2E)-(4-chloro-3-methyl-2-butenyl)]amino]-5-(tert-butyldimethylsilyloxy)-2-penten-1-ol(794518-65-3)
• EPA Substance Registry System: (2E,4S)-4-[N-benzyl-N-[(2E)-(4-chloro-3-methyl-2-butenyl)]amino]-5-(tert-butyldimethylsilyloxy)-2-penten-1-ol(794518-65-3)

Safety Data

• Hazardous Substances Data: 794518-65-3(Hazardous Substances Data)

Upstream product

• 794518-63-1 (2E,4S)-4-[N-benzyl-N-[(2E)-(4-chloro-3-methyl-2-butenyl)]amino]-5-(tert-butyldimethylsilyloxy)-2-pentenoic acid ethyl ester 
• 794518-61-9 (2E,4S)-4-[N-benzyl-N-[(E)-(3-methyl-4-triethylsilyloxy)-2-butenyl]amino]-5-(tert-butyldimethylsilyloxy)-2-pentenoic acid ethyl ester 
• 794518-60-8 (2S)-2-(benzyl{(2E)-3-methyl-4-[(triethylsilyl)oxy]-2-butenyl}amino)-3-{[tert-butyl(dimethyl)silyl]oxy}-1-propanol 
• 794518-62-0 (2E,4S)-4-[N-benzyl-N-[(2E)-(4-hydroxy-3-methyl-2-butenyl)]amino]-5-(tert-butyldimethylsilyloxy)-2-pentenoic acid ethyl ester 
• 794518-57-3 methyl (2R)-2-(benzylamino)-3-{[tert-butyl(dimethyl)silyl]oxy}propanoate 
• 794518-73-3 {[(2E)-4-bromo-2-methyl-2-butenyl]oxy}(triethyl)silane 
• 852946-25-9 (2E)-3-methyl-4-[(triethylsilyl)oxy]-2-buten-1-ol 
• 123639-56-5 methyl (2R)-2-(benzylamino)-3-hydroxypropanoate 

Downstream Products

• 487-79-6 (-)-kainic acid 
• 794518-71-1 [2R,3R,3(1Z),4R]-1-benzyl-2-[(tert-butyldimethylsilyloxy)methyl]-3-[2-(N,N-diisopropylcarbamoyloxy)ethenyl]-4-(1-methylethenyl)pyrrolidine 
• 794518-67-5 [2R,3S,3(1Z),4S]-1-benzyl-2-[(tert-butyldimethylsilyloxy)methyl]-3-[2-(N,N-diisopropylcarbamoyloxy)ethenyl]-4-(1-methylethenyl)pyrrolidine 
• 794518-68-6 Diisopropyl-carbamic acid (E)-2-[(2S,3R,4S)-1-benzyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-isopropenyl-pyrrolidin-3-yl]-1-methylsulfanyl-vinyl ester 
• 794518-66-4 (2E,4S)-4-[N-benzyl-N-[(2E)-(4-chloro-3-methyl-2-butenyl)]amino]-5-(tert-butyldimethylsilyloxy)-2-penten-1-yl N,N-diisopropylcarbamate 

Relevant articles and documents

Novel approach to the (-)-sparteine-mediated synthesis of kainoids: Total synthesis of (-)-α-kainic acid by (-)-sparteine-mediated deprotonation

We report a new synthesis of kainoids via allyllithium compounds using an intramolecular cycloalkylation as the key step. Preparation of different substituted pyrrolidines was carried out by using carbamates, that react with the chiral base n-BuLi/(-)-sparteine with strong selection between the diastereotopic protons adjacent to the carbamate group in favour for the pro-S proton. (-)-α-Kainic acid was synthetized from D-serine methyl ester hydrochloride, based on a (-)-sparteine-mediated asymmetric deprotonation of an intermediate carbamate that, by stereospecific anti-SN′S E′ intramolecular cycloalkylation, leads to the pyrrolidine ring precursor of (-)-α-kainic acid, in high yield and diastereoselectivity. Related approaches, starting from L-glutamic acid failed. The intermediate pyrrolidine was further transformed to (-)-α-kainic in three steps. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.