1314808-96-2

Upstream product

• 570371-48-1 (S)-3-(benzyloxy)-2,2-dimethylpent-4-enal 
• 4301-14-8 acetylenemagnesium bromide 
• 277317-84-7 (2R/S,3R)-3-(Benzyloxy)tetrahydro-4,4-dimethylfuran-2-ol 
• 20374-33-8 (R)-(+)-3-(Benzyloxy)-4,5-dihydro-4,4-dimethyl-furan-2(3H)-on 
• 147252-93-5 (3S)-3-(benzyloxy)-2,2-dimethyl-4-penten-1-ol 

Downstream Products

• 1314809-05-6 (2R,6S)-6-[(4S)-4-benzyloxy-3,3-dimethyl-2-oxohex-5-enyl]-4-methylene-2-[(2-trimethylsilylethoxy)methoxy]methyltetrahydropyran 
• 1314809-07-8 (2R,6R)-6-[(4S)-4-benzyloxy-3,3-dimethyl-2-oxohex-5-enyl]-4-methylene-2-[(2-trimethylsilylethoxy)methoxy]methyltetrahydropyran 
• 1314809-10-3 (2R,6R)-6-[(4S)-4-benzyloxy-3,3-dimethyl-2-oxohex-5-enyl]-2-[(tert-butyldiphenylsilyloxy)methyl]-4-methylidenetetrahydropyran 
• 1314809-09-0 (2R,6S)-6-[(4S)-4-benzyloxy-3,3-dimethyl-2-oxohex-5-enyl]-2-[(tert-butyldiphenylsilyloxy)methyl]-4-methylenetetrahydropyran 
• 1314809-11-4 (2R,6S)-6-[(4S)-4-benzyloxy-3,3-dimethyl-2-oxohex-5-enyl]-2-[(tert-butyldiphenylsilyloxy)methyl]-4-methyl-4,1''-epoxytetrahydropyran 
• 470470-59-8 (5S)-5-benzyloxy-4,4-dimethylhept-6-en-1-yn-3-one 
• 470470-60-1 (3S,11R,6E)-3-benzyloxy-11-(tert-butyldimethylsilyloxy)-4,4-dimethyl-12-[(2-trimethylsilylethoxy)methoxy]-9-[(E)-trimethylsilylmethylidene]dodeca-1,6-dien-5-one 

Relevant academic research and scientific papers

Synthesis of 2,6-cis-disubstituted 4-methylenetetrahydropyrans by oxy-Michael addition

The combination of an 'ene' reaction between a 2-(2-trialkylsilyloxyalkyl) prop-2-enyl(trimethyl)silane and an alk-1-yn-3-one mediated by zinc(II) iodide, and an intramolecular oxy-Michael reaction, provides an efficient synthesis of cis-2,6-disubstituted 4-methylenetetrahydropyrans of interest in the context of a synthesis of bryostatins. The stereoselective formation of (E)-vinylsilanes in the 'ene' reaction is of interest.