792913-06-5

Basic information

• Product Name: 3-((2R,3R,5R)-tetrahydro-3-methyl-5-(6-methyloctyl)-2H-pyran-2-yl)-4-hydroxy-5-phenyl-6-chloropyridin-2(1H)-one
• Synonyms: 3-((2R,3R,5R)-tetrahydro-3-methyl-5-(6-methyloctyl)-2H-pyran-2-yl)-4-hydroxy-5-phenyl-6-chloropyridin-2(1H)-one
• CAS NO: 792913-06-5
• Molecular Weight: 446.03
• Mol File: 792913-06-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3-((2R,3R,5R)-tetrahydro-3-methyl-5-(6-methyloctyl)-2H-pyran-2-yl)-4-hydroxy-5-phenyl-6-chloropyridin-2(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-((2R,3R,5R)-tetrahydro-3-methyl-5-(6-methyloctyl)-2H-pyran-2-yl)-4-hydroxy-5-phenyl-6-chloropyridin-2(1H)-one(792913-06-5)
• EPA Substance Registry System: 3-((2R,3R,5R)-tetrahydro-3-methyl-5-(6-methyloctyl)-2H-pyran-2-yl)-4-hydroxy-5-phenyl-6-chloropyridin-2(1H)-one(792913-06-5)

Safety Data

• Hazardous Substances Data: 792913-06-5(Hazardous Substances Data)

Upstream product

• 792913-04-3 (R)-6-[2,4-bis-(tert-butyldimethylsilanyloxy)-5-phenyl-6-chloropyridin-3-yl]-(R)-5-methyltetrahydropyran-3-one 
• 792913-03-2 6-[2,4-bis-(tert-butyl-dimethyl-silanyloxy)-6-chloro-5-phenyl-pyridin-3-yl]-6H-pyran-3-one 
• 792913-02-1 (4bS,8aS)-2-Chloro-1-phenyl-3,4b,8,8a-tetrahydro-5,9-dioxa-3-aza-fluorene-4,7-dione 
• 663176-49-6 (R,E)-6-methylocta-2,7-dien-1-ol 
• 648409-56-7 5-((S)-6-methyloctylsulfonyl)-1-phenyl-1H-tetrazol 
• 188670-22-6 (S)-5-oxo-5,6-dihydro-2H-pyran-2-yl acetate 
• 176221-88-8 (R,E)-methyl 6-methylocta-2,7-dienoate 
• 110453-78-6 (S)-(+)-6-methyl-1-octanol 
• 32265-03-5 6-chloro-4-hydroxy-5-phenyl(1H)-pyridin-2-one 
• 792913-05-4 3-((2R,3R)-tetrahydro-3-methyl-5-(6-methyloctyliden)-2H-pyran-2-yl)-4-hydroxy-5-phenyl-6-chloropyridin-2(1H)-one 

Relevant articles and documents

Synthesis and evaluation of the antitumor agent TMC-69-6H and a focused library of analogs

A concise, efficient and flexible total synthesis of the potent antitumor agent TMC-69-6H (2) is described. Key steps involve the palladium catalyzed regioselective addition of 4-hydroxy-2-pyridone 5 to pyranyl acetate 6 which is accompanied by a spontaneous 1,4-addition of the phenolic -OH group to the emerging enone to give the tricyclic product 7 in excellent yield. When this reaction is carried out with optically enriched (S)-6 (conveniently prepared by a lipase catalyzed kinetic dynamic resolution) in the presence of the chiral ligand (S,S)-12 and allylpalladium chloride dimer, the ensuing matched situation delivers the key building block (-)-7 in 96% ee. Its further elaboration into 2 involves a Julia-Kocienski olefination with tetrazolylsulfone 19 and a final N-oxidation effected by the peroxomolybdenum complex [(pyridine)MoO 5(HMPA)] to form the hydroxamic acid motif. The flexibility inherent to this route allows for the preparation of a focused library of analogues for biochemical evaluation. The results obtained show that N-hydroxy-2-pyridone derivatives constitute a promising new class of selective phosphatase inhibitors. In contrast to previous reports in the literature, however, TMC-69-6H and congeners are found to exhibit pronounced activities against the tyrosine protein phosphatase PTB1B, the dual specific phosphatase VHR, and the serine/threonine phosphatase PP1, while being only weak inhibitors for the dual specific phosphatases Cdc25 A and B. Two key intermediates of the synthesis route have been characterized by X-ray crystallography. Graphical Abstract.