1244033-28-0

Basic information

• Product Name: (+)-4-(2-((2S,6R)-6-(4-methoxyphenyl)tetrahydro-2H-pyran-2-yl)ethyl)phenyl acetate
• Synonyms: (+)-4-(2-((2S,6R)-6-(4-methoxyphenyl)tetrahydro-2H-pyran-2-yl)ethyl)phenyl acetate
• CAS NO: 1244033-28-0
• Molecular Weight: 354.446
• Mol File: 1244033-28-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (+)-4-(2-((2S,6R)-6-(4-methoxyphenyl)tetrahydro-2H-pyran-2-yl)ethyl)phenyl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-4-(2-((2S,6R)-6-(4-methoxyphenyl)tetrahydro-2H-pyran-2-yl)ethyl)phenyl acetate(1244033-28-0)
• EPA Substance Registry System: (+)-4-(2-((2S,6R)-6-(4-methoxyphenyl)tetrahydro-2H-pyran-2-yl)ethyl)phenyl acetate(1244033-28-0)

Safety Data

• Hazardous Substances Data: 1244033-28-0(Hazardous Substances Data)

Upstream product

• 340825-63-0 (R)-2-(4-benzyloxyphenethyl)oxirane 
• 68486-77-1 3-(4-(benzyloxy)phenyl)propanal 
• 79407-40-2 2-{2-[4-(benzyloxy)phenyl]ethyl}oxirane 
• 6272-45-3 4-benzyloxycinnamic acid 
• 123-08-0 4-hydroxy-benzaldehyde 
• 134721-17-8 1-(benzyloxy)-4-(but-3-en-1-yl)benzene 
• 61440-45-7 3-[4-(benzyloxy)phenyl]propan-1-ol 
• 4397-53-9 p-benzyloxybenzaldehyde 
• 108-24-7 acetic anhydride 
• 871809-93-7 (+)-(3R)-1-[4-(benzyloxy)phenyl]hex-5-en-3-ol 
• 58608-97-2 3-(4-benzyloxyphenyl)propionic acid benzyl ester 
• 501-97-3 4-hydroxyphenylpropionic acid 

Relevant articles and documents

Catalytic δ-hydroxyalkynone rearrangement in the stereoselective total synthesis of centrolobine, engelheptanoxides A and C and analogues

A catalytic stereoselective total synthesis of centrolobine and engelheptanoxides A and C has been completed via a metal-free catalytic δ-hydroxyalkynone rearrangement to 2,3-dihydro-4H-pyran-4-one and diastereoselective hydrogenation to the all syn-2,4,6-trisubstituted pyran strategy. The onliest required chirality was introduced by Jacobsen kinetic resolution, which further directed the diastereoselective hydrogenation. A first stereoselective synthesis of engelheptanoxide A is also accomplished. The analogues and derivatives of centrolobine and engelheptanoxides prepared were evaluated for antitubercular activity against M. tuberculosis H37Rv ATCC 27294.

The biomimetic synthesis and final structure determination of (+)- and (-)-centrolobine, naturally occurring diarylheptanoid 2,6-cis-disubstituted tetrahydro-2H-pyrans

The enantiomerically pure title compounds were prepared by oxidative cyclization of their optically active diarylheptanoid precursors. The approach is considered as a biomimetic phenol oxidation via an intermediate quinone methide. The absolute configuration of the precursors is retained, and the transition state adopts the sterically most favorable diequatorial arrangement of the 2,6-substituents to afford the cis-configured natural products. The outcome unambiguously establishes the absolute configurations and the correlation with the chiroptical data. In addition, a problem of regioisomerism that had not been discussed before was solved, and the original assignment of the position of the MeO group in the natural centrolobines could be confirmed. As such the results are the experimental evidence for the corrections of long-term inconsistencies we had postulated in an earlier review article.