949890-75-9

Basic information

• Product Name: (-)-(S)-3-(benzyloxycarbonylamino-methyl)-5-methyl-hexanoic acid
• Synonyms: (-)-(S)-3-(benzyloxycarbonylamino-methyl)-5-methyl-hexanoic acid
• CAS NO: 949890-75-9
• Molecular Weight: 293.363
• Mol File: 949890-75-9.mol

Chemical Properties

• CAS DataBase Reference: (-)-(S)-3-(benzyloxycarbonylamino-methyl)-5-methyl-hexanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-(S)-3-(benzyloxycarbonylamino-methyl)-5-methyl-hexanoic acid(949890-75-9)
• EPA Substance Registry System: (-)-(S)-3-(benzyloxycarbonylamino-methyl)-5-methyl-hexanoic acid(949890-75-9)

Safety Data

• Hazardous Substances Data: 949890-75-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
(-)-(S)-3-(benzyloxycarbonylamino-methyl)-5-methyl-hexanoic acid serves as a crucial precursor in the synthesis of various pharmaceuticals. Its unique structure allows it to be a building block for developing drugs that can effectively target the central nervous system, addressing a wide range of neurological disorders and conditions.
Used in Cancer Therapy Research:
(-)-(S)-3-(benzyloxycarbonylamino-methyl)-5-methyl-hexanoic acid has garnered interest for its potential use in cancer therapy. The biological activity of the (S)-enantiomer suggests that it may play a role in the development of novel treatments for cancer. Ongoing research is focused on understanding its mechanisms of action and its potential to be incorporated into therapeutic strategies against various types of cancer.
Used in Medicinal Chemistry:
(-)-(S)-3-(benzyloxycarbonylamino-methyl)-5-methyl-hexanoic acid is a valuable tool in medicinal chemistry. Its unique properties and structure make it an ideal candidate for further exploration and development in the creation of new drugs and therapies. Researchers are continuously investigating its potential applications to expand the horizons of medical treatments and improve patient outcomes.

Upstream product

• 949890-73-7 (-)-(S)-3-(benzyloxycarbonylamino-methyl)-5-methyl-hexanoic acid 3-phenyl-allyl ester 
• 949890-69-1 (-)-(R)-3-isobutyl-pentanedioic acid mono-(3-phenyl-allyl) ester 
• 185815-59-2 3-isobutylglutaric anhydride 
• 1432752-42-5 (R)-3-(2-(benzylthio)-2-oxoethyl)-5-methylhexanoic acid 
• 1432752-43-6 (S)-S-benzyl 3-((((benzyloxy)carbonyl)amino)methyl)-5-methylhexanethioate 

Downstream Products

• 148553-50-8 pregabilin 
• 1224700-49-5 C₂₆H₃₃N₃O₃ 
• 1224700-48-4 C₂₂H₃₄N₂O₈ 
• 1224700-50-8 C₂₆H₃₃N₃O₄ 
• 1224700-51-9 C₂₆H₃₈N₂O₃ 

Relevant articles and documents

Preparation method for asymmetrical synthesis of pregabalin

The invention discloses a preparation method for asymmetric synthesis of pregabalin.The preparation method includes: using 3-isobutylglutaric anhydride as a starting raw material; under catalytic action of chiral thiourea ammonium salt, enabling the starting raw material to be in asymmetric alcoholysis with mercaptan to generate mercaptide; enabling mercaptide to react with diphenylphosphoryl azide and benzyl alcohol sequentially to generate benzyloxy carbonyl methyl mercaptide; obtaining pregabalin through hydrolysis and hydrogenation reduction.The synthetic method is adopted to synthesize pregabalin, asymmetric catalysis is adopted to synthesize a key intermediate, a chemical resolution reagent is not used, total yield is greater than 50%, and ee value is greater than 94%.The preparation method has the advantages of novel synthesis path, few steps, mild reaction condition and the like.

Highly enantioselective thiolysis of prochiral cyclic anhydrides catalyzed by amino alcohol bifunctional organocatalysts and its application to the synthesis of pregabalin

Asymmetric thiolysis of prochiral cyclic anhydrides was achieved with our developed chiral sulfonamide and squaramide bifunctional organocatalysts based on amino alcohol scaffolds. The corresponding thioesters were obtained in high yields with excellent enantioselectivities. The usefulness of this methodology was demonstrated in the enantioselective synthesis of pregabalin. A highly enantioselective thiolysis of prochiral cyclic anhydrides was achieved with chiral sulfonamide bifunctional organocatalysts based on an amino alcohol scaffold. The usefulness of this methodology was demonstrated through a synthetic application to pregabalin. Copyright

Synthesis, characterization and in vitro pharmacology of novel pregabalin derivatives

A series of novel pregabalin derivatives were synthesized starting from N-protected pregabalin, different amino sugars, adamantylamine, serotonin and tryptamine. New compounds were spectroscopically characterized and in vitro tested on gabapentin receptor binding assay. The serotonin-pregabalin adduct showed significant binding effect and its IC50 value was determined.

An efficient synthesis of (S)-3-aminomethyl-5-methylhexanoic acid (Pregabalin) via quinine-mediated desymmetrization of cyclic anhydride

A highly enantioselective synthesis of (S)-3-aminomethyl-5-methylhexanoic acid 1 (Pregabalin) is reported. The key step of the synthesis is a quinine-mediated ring opening of 3-isobutylglutaric anhydride with cinnamyl alcohol. A Curtius rearrangement and subsequent deprotection provides 1 in high yield and excellent enantiomeric excess.