116315-75-4

Upstream product

• 5162-44-7 1-bromo-4-butene 
• 115114-87-9 (2R)-2-(2-benzyloxyethyl)oxirane 
• 71998-69-1 (S)-4-benzyloxy-1,2-butanediol 
• 100-39-0 benzyl bromide 
• 70388-33-9 4-benzyloxybut-1-ene 
• 94426-72-9 2-(2-(benzyloxy)ethyl)oxirane 
• 116315-73-2 (S)-4-phenylmethoxybutane-1,2-diyl dimethane sulphonate 
• 69985-32-6 (R)-4-phenylmethoxy-1,2-butanediol 
• 116315-74-3 (R)-4-phenylmethoxybutane-1,2-diyl diacetate 

Downstream Products

• 1200-22-2 (R)-1,2-dithiolane-3-pentanoic acid 
• 116315-79-8 (S)-methyl 6,8-diphenylmethoxyoctanoate 
• 116315-77-6 (S)-6,8-diphenylmethoxyoctan-1-ol 
• 116315-78-7 (S)-6,8-diphenylmethoxyoctanoic acid 
• 116349-04-3 (6S)-(-)-methyl 6,8-dihydroxyoctanoate 
• 116315-76-5 (S)-6,8-diphenylmethoxyoct-1-ene 

Relevant academic research and scientific papers

An efficient, highly enantioenriched route to L-carnitine and α-lipoic acid via hydrolytic kinetic resolution

A general and practical approach for the synthesis of C-4 chiral building blocks using Jacobsen's hydrolytic kinetic resolution technique to resolve terminal epoxides and diols in high enantiomeric excess and excellent yields is described. The utilization of these building blocks for the synthesis of biologically important natural products L-carnitine and α-lipoic acid is illustrated. Georg Thieme Verlag Stuttgart.

SYNTHESES OF α-(R)-AND α-(S)-LIPOIC ACID FROM (S)-MALIC ACID

(S)-Malic acid has been converted into α-(R)-and α-(S)-lipoic acid via (R)-and (S)-(2-phenylmethoxyethyl)oxirane .The (R)-oxirane (2a) was cleaved with but-3-enylmagnesium bromide (cuprate catalysis) to give (S)-1-(phenylmethoxy)oct-7-en-3-ol (4a).This was converted into methyl (S)-6,8-dihydroxyoctanoate (5a), the di-O-methanesulphonate (6a) of which was treated with sodium sulphide and sulphur in dimethylformamide to yield methyl α-(R)-lipoate (7a), that was saponified to α-(R)-lipoic acid (1a).The (S)-oxirane (2b) was similarly converted into α-(S)-lipoic acid (1b).