419541-71-2

Upstream product

• 18388-03-9 2-chloromethyl-3-trimethylsilyl-1-propene 
• 112897-03-7 3-(tert-butyldiphenylsilyloxy)-1-propanal 
• 129601-00-9 3-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)propionitrile 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 164662-96-8 1-trimethylsilyl-2-(tributylstannyl)methyl-2-propene 

Downstream Products

• 419541-63-2 1-(2-{(6R,2S)-4-methylene-6-[(phenylmethoxy)methyl](3,5,6-trihydro-2H-pyran-2-yl)}ethoxy)-2,2-dimethyl-1,1-diphenyl-1-silapropane 
• 858917-87-0 2-(6-{(1E,4R)-5-[(4-methoxyphenyl)methoxy]-2-methyl-2-(1,1,2,2-tetramethyl-1-silapropoxy)pent-1-enyl}(2S,6R)-4-methylene-2,3,5,6-tetrahydropyran-2-yl)ethan-1-ol 
• 858917-33-6 {(2S,6R)-6-[(E)-(R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2-methyl-pent-1-enyl]-4-methylene-tetrahydro-pyran-2-yl}-acetaldehyde 
• 858917-26-7 (4E,2R)-5-{(6S,2R)-6-[2-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)ethyl]-4-methylene-(2,3,5,6-tetrahydropyran-2-yl)}-1-[(4-methoxyphenyl)methoxy]-4-methyl-2-(1,1,2,2-tetramethyl-1-silapropoxy)pent-4-ene 
• 854931-26-3 {2-[(2S,6R)-6-((E)-3-{(S)-6-[(2R,3R)-3-Benzyloxymethoxy-2-(4-methoxy-benzyloxy)-butyl]-5,6-dihydro-4H-pyran-2-yl}-3-methyl-but-1-enyl)-4-methylene-tetrahydro-pyran-2-yl]-ethoxy}-tert-butyl-diphenyl-silane 

Relevant academic research and scientific papers

Enantioselective Synthesis of cis-2,6-Disubstituted-4-methylene Tetrahydropyrans via Chromium Catalysis?

Enantioenriched 2,6-disubstituted 4-methylene tetrahydropyrans have been obtained via a two-step sequence consisting of a highly enantioselective chromium-catalyzed carbonyl 2-(trimethylsilyl methyl)allylation and Prins cyclization. Commercially available (2-(chloromethyl)allyl)trimethylsilane serves as the bifunctional linchpin to combine two aldehydes to assemble the 2,6-disubstituted pyrans. A variety of functional groups are compatible under the mild reaction conditions. The synthetic utility of this methodology was demonstrated by the asymmetric synthesis of 16 examples of homoallylic alcohol and 8 examples of 2,6-disubstituted 4-methylene tetrahydropyrans, including an advanced intermediate which could be transformed to natural product centrolobine via a known procedure.

Total synthesis of (+)-dactylolide

(Chemical Equation Presented) The development of an approach leading to the total synthesis of dactylolide is described. The key features of this route include a catalytic asymmetric allylation, a diastereoselective pyran annulation, and a Horner-Wadswort

Pyran annulation: asymmetric synthesis of 2,6-disubstituted-4-methylene tetrahydropyrans.

[reaction: see text] A reaction process for the asymmetric construction of a variety of cis or trans disubstituted pyrans is described. This sequences allows for the asymmetric convergent union of two aldehydes with silyl-stannane reagent 1 in a two-step