118992-01-1

Upstream product

• 111427-82-8 2-((4R,5R,6R)-4-Benzyloxymethyl-2,2-dimethyl-6-octyl-[1,3]dioxan-5-yl)-ethanol 
• 17049-49-9 octylmagnesium bromide 
• 111427-77-1 (S)-3-((R)-2-Benzyloxy-1-hydroxy-ethyl)-dodec-1-en-4-one 
• 111427-75-9 [1-((2R,3S)-3-Benzyloxymethyl-oxiranyl)-1-vinyl-nonyloxy]-trimethyl-silane 
• 111427-79-3 (2R,3R,4R)-1-Benzyloxy-3-vinyl-dodecane-2,4-diol 
• 111427-81-7 (4R,5R,6R)-4-Benzyloxymethyl-2,2-dimethyl-6-octyl-5-vinyl-[1,3]dioxane 
• 111468-00-9 2-((4R,5R,6S)-4-Benzyloxymethyl-2,2-dimethyl-6-octyl-[1,3]dioxan-5-yl)-ethanol 
• 111467-98-2 (2R,3R,4S)-1-Benzyloxy-3-vinyl-dodecane-2,4-diol 
• 111467-99-3 (4R,5R,6S)-4-Benzyloxymethyl-2,2-dimethyl-6-octyl-5-vinyl-[1,3]dioxane 
• 111427-80-6 (2R,3R,4S)-1-Benzyloxy-3-(1-trimethylsilanyl-vinyl)-dodecane-2,4-diol 
• 111427-76-0 3-((2R,3S)-3-Benzyloxymethyl-oxiranyl)-2-trimethylsilanyl-undec-1-en-3-ol 
• 111427-78-2 (S)-3-((R)-2-Benzyloxy-1-hydroxy-ethyl)-2-trimethylsilanyl-dodec-1-en-4-one 
• 112164-80-4 (2S,3R)-2-Benzyloxymethyl-3-[1-trimethylsilanyloxy-1-(1-trimethylsilanyl-vinyl)-nonyl]-oxirane 
• 118992-05-5 3-((2R,3S)-3-Benzyloxymethyl-oxiranyl)-undec-1-en-3-ol 

Downstream Products

• 111427-83-9 ((4R,5R,6R)-4-Benzyloxymethyl-2,2-dimethyl-6-octyl-[1,3]dioxan-5-yl)-acetic acid ethyl ester 
• 118992-02-2 ((4R,5R,6R)-4-Benzyloxymethyl-2,2-dimethyl-6-octyl-[1,3]dioxan-5-yl)-acetic acid 
• 20223-76-1 (-)-avenaciolide 
• 111468-01-0 ((4R,5R,6S)-4-Benzyloxymethyl-2,2-dimethyl-6-octyl-[1,3]dioxan-5-yl)-acetic acid ethyl ester 
• 118992-02-2 ((4R,5R,6S)-4-Benzyloxymethyl-2,2-dimethyl-6-octyl-[1,3]dioxan-5-yl)-acetic acid 
• 33644-09-6 (-)-isoavenaciolide 

Relevant academic research and scientific papers

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

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