181053-79-2

Upstream product

• 58479-61-1 tert-butylchlorodiphenylsilane 
• 181053-78-1 ethyl (2E,4E,6Z)-8-hydroxy-2,6-dimethylocta-2,4,6-trienoate 
• 181053-71-4 (2E,6Z)-8-(tert-Butyl-dimethyl-silanyloxy)-4-dimethylamino-2,6-dimethyl-octa-2,6-dienoic acid ethyl ester 
• 181053-74-7 (3E,6Z)-8-(tert-Butyl-dimethyl-silanyloxy)-2-(N,N-dimethyl-aminooxy)-2,6-dimethyl-octa-3,6-dienoic acid ethyl ester 
• 181053-73-6 ethyl (2E,4E,6Z)-8-tert-butyldimethylsiloxy-2,6-dimethylocta-2,4,6-trienoate 

Downstream Products

• 463302-50-3 9-(2',6',6'-trimethylcyclohex-1'-enyl)-8-acetoxy-1-tert-butyldiphenylsiloxy-3,7-dimethyl-9-(p-tolylsulfonyl)nona-2Z,4E,6E-triene 
• 181053-77-0 9-(2',6',6'-trimethylcyclohex-1'-enyl)-8-acetoxy-3,7-dimethyl-9-(p-tolylsulfonyl)nona-2Z,4E,6E-trien-1-ol 
• 181053-76-9 (2E,4E,6Z)-8-tert-butyldiphenylsiloxy-2,6-dimethylocta-2,4,6-trienal 
• 2052-63-3 2-cis-Vitamin-A 
• 181053-80-5 (2E,4E,6Z)-8-tert-butyldiphenylsiloxy-2,6-dimethylocta-2,4,6-trien-1-ol 

Relevant academic research and scientific papers

Highly Z selective synthesis of functionalized monoterpenoids via N-ylide [2,3]sigmatropic rearrangement and its application to 13-cis-retinol

Highly stereoselective elongation of a functionalized E isoprene unit on the Z terminal methyl of prenol was achieved by the N-ylide rearrangement of N-tiglyl-β-methallyldimethyl-ammonium salt. (E,Z)-Rearrangement product was converted into 13-cis-retinol via useful conjugated triene isoprenoid synthon.

Stereocontrolled synthesis of acyclic terpenoids via N-ylide [2,3]rearrangement of ammonium salts with the stereodefined isoprene unit

Stereocontrolled elongation of a functionalized isoprene unit on the E or Z terminal methyl of terpenoids was achieved by N-ylide rearrangement of the common ammonium salts under selected reaction conditions. A 1,5-diene or conjugated triene skeleton can be furnished by reductive or oxidative removal of the amino group of the rearrangement product, respectively. As an application to natural-product synthesis, all-(E)-terpenoid (E)-11d and (E,Z)-terpenoid (Z)-11c were converted into β-sinensal and (13Z)-retinol, respectively. General aspects of these transformations and a plausible transition state for the N-ylide rearrangement are discussed.