111427-79-3

Upstream product

• 111427-77-1 (S)-3-((R)-2-Benzyloxy-1-hydroxy-ethyl)-dodec-1-en-4-one 
• 118992-05-5 3-((2R,3S)-3-Benzyloxymethyl-oxiranyl)-undec-1-en-3-ol 
• 111427-74-8 1-((2R,3S)-3-Benzyloxymethyl-oxiranyl)-nonan-1-one 
• 111427-75-9 [1-((2R,3S)-3-Benzyloxymethyl-oxiranyl)-1-vinyl-nonyloxy]-trimethyl-silane 
• 17049-49-9 octylmagnesium bromide 

Downstream Products

• 118992-02-2 ((4R,5R,6R)-4-Benzyloxymethyl-2,2-dimethyl-6-octyl-[1,3]dioxan-5-yl)-acetic acid 
• 111427-83-9 ((4R,5R,6R)-4-Benzyloxymethyl-2,2-dimethyl-6-octyl-[1,3]dioxan-5-yl)-acetic acid ethyl ester 
• 118992-01-1 ((4R,5R,6R)-4-Benzyloxymethyl-2,2-dimethyl-6-octyl-[1,3]dioxan-5-yl)-acetaldehyde 
• 111427-82-8 2-((4R,5R,6R)-4-Benzyloxymethyl-2,2-dimethyl-6-octyl-[1,3]dioxan-5-yl)-ethanol 
• 20223-76-1 (-)-avenaciolide 
• 111427-81-7 (4R,5R,6R)-4-Benzyloxymethyl-2,2-dimethyl-6-octyl-5-vinyl-[1,3]dioxane 

Relevant academic research and scientific papers

STEREO-DIVERGENT ASYMMETRIC TOTAL SYNTHESIS OF AVENACIOLIDE AND ISOAVENACIOLIDE. COMPLETE REVERSAL OF STEREOSELECTIVITY IN REDUCTION OF 2-VINYL ALDOLS WITH / WITHOUT TRIMETHYLSILYL DIRECTING GROUP

Stereo-divergent asymmetric total synthesis of avenaciolide and isoavenaciolide was achieved via 1,2-rearrangement of chiral epoxyalcohol derivatives, where complete reversal of stereoselectivity with / without the TMS-directing group in the reduction of

Silicon-Directed Stereoselective Synthesis of 2-vinyl-1,3-diols. Stereo-Divergence with and without the silyl Group Related to the Synthesis of Avenaciolide and Isoavenaciolide

A flexible approach to the stereoisomers of 2-vinyl-1,3-diols via the reduction of 2-vinyl aldols is described.The presence of the TMS group at the α-position of the vinyl group firmly establishes the syn relationship between the newly-formed hydroxyl gro