477284-03-0

Upstream product

• 477284-11-0 4-{(2S,4R,6S)-6-[2-(4-Benzyloxy-phenyl)-ethyl]-4-bromo-tetrahydro-pyran-2-yl}-phenol 
• 74-88-4 methyl iodide 
• 123-11-5 4-methoxy-benzaldehyde 
• 767330-04-1 (-)-(3S)-1-[4-(benzyloxy)phenyl]hex-5-en-3-ol 
• 80459-48-9 4-tosyloxybenzaldehyde 
• 477284-01-8 Acetic acid 3-(4-benzyloxy-phenyl)-1-{(S)-1-[4-(toluene-4-sulfonyloxy)-phenyl]-but-3-enyloxy}-propyl ester 
• 477284-02-9 Toluene-4-sulfonic acid 4-{(2S,4R,6S)-6-[2-(4-benzyloxy-phenyl)-ethyl]-4-bromo-tetrahydro-pyran-2-yl}-phenyl ester 
• 477284-08-5 3-(4-Benzyloxy-phenyl)-propionic acid (S)-1-[4-(toluene-4-sulfonyloxy)-phenyl]-but-3-enyl ester 
• 477284-07-4 Toluene-4-sulfonic acid 4-((S)-1-hydroxy-but-3-enyl)-phenyl ester 
• 50463-48-4 3-(4-benzyloxyphenyl)propanoic acid 
• 68486-77-1 3-(4-(benzyloxy)phenyl)propanal 

Downstream Products

• 30358-99-7 Centrolobin 
• 477284-09-6 (2S,6R)-6-[2-[4-(benzyloxy)phenyl]ethyl]-2-[4-(methoxy)phenyl]tetrahydropyran 

Relevant academic research and scientific papers

Prins cyclizations in silyl additives with suppression of epimerization: Versatile tool in the synthesis of the tetrahydropyran backbone of natural products

(Chemical Equation Presented) A catalytic Prins cyclization reaction has been developed. The involvement of trimethylsilyl halides offers a versatile route to the formation of cis-4-halo-2,6-disubstituted tetrahydropyran rings. The problem of epimerizatio

Synthesis of (-)-centrolobine by Prins cyclizations that avoid racemization.

[formula: see text] The segment-coupling Prins cyclization avoids two of the problems common to other Prins cyclization protocols: side-chain exchange and partial racemization by reversible 2-oxonia Cope rearrangement. Model studies demonstrate the stereochemical fidelity of Prins cyclizations using alpha-acetoxy ethers compared with direct aldehyde-alcohol Prins reactions. Furthermore, we propose a mechanism for the racemization observed in some intermolecular Prins cyclizations. Two straightforward syntheses of optically pure (-)-centrolobine highlight the utility of Prins cyclizations.