193811-96-0

Basic information

• Product Name: Toluene-4-sulfonic acid (E)-(R)-11-{(2R,5R,2'R,5'R)-5'-[(E)-(R)-11-hydroxy-1-(2-trimethylsilanyl-ethoxymethoxy)-undec-2-enyl]-octahydro-[2,2']bifuranyl-5-yl}-11-(2-trimethylsilanyl-ethoxymethoxy)-undec-9-enyl ester
• Synonyms: Toluene-4-sulfonic acid (E)-(R)-11-{(2R,5R,2'R,5'R)-5'-[(E)-(R)-11-hydroxy-1-(2-trimethylsilanyl-ethoxymethoxy)-undec-2-enyl]-octahydro-[2,2']bifuranyl-5-yl}-11-(2-trimethylsilanyl-ethoxymethoxy)-undec-9-enyl ester
• CAS NO: 193811-96-0
• Molecular Weight: 925.469
• Mol File: 193811-96-0.mol

Chemical Properties

• CAS DataBase Reference: Toluene-4-sulfonic acid (E)-(R)-11-{(2R,5R,2'R,5'R)-5'-[(E)-(R)-11-hydroxy-1-(2-trimethylsilanyl-ethoxymethoxy)-undec-2-enyl]-octahydro-[2,2']bifuranyl-5-yl}-11-(2-trimethylsilanyl-ethoxymethoxy)-undec-9-enyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Toluene-4-sulfonic acid (E)-(R)-11-{(2R,5R,2'R,5'R)-5'-[(E)-(R)-11-hydroxy-1-(2-trimethylsilanyl-ethoxymethoxy)-undec-2-enyl]-octahydro-[2,2']bifuranyl-5-yl}-11-(2-trimethylsilanyl-ethoxymethoxy)-undec-9-enyl ester(193811-96-0)
• EPA Substance Registry System: Toluene-4-sulfonic acid (E)-(R)-11-{(2R,5R,2'R,5'R)-5'-[(E)-(R)-11-hydroxy-1-(2-trimethylsilanyl-ethoxymethoxy)-undec-2-enyl]-octahydro-[2,2']bifuranyl-5-yl}-11-(2-trimethylsilanyl-ethoxymethoxy)-undec-9-enyl ester(193811-96-0)

Safety Data

• Hazardous Substances Data: 193811-96-0(Hazardous Substances Data)

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 193811-95-9 (E)-(R)-11-{(2R,5R,2'R,5'R)-5'-[(E)-(R)-11-Hydroxy-1-(2-trimethylsilanyl-ethoxymethoxy)-undec-2-enyl]-octahydro-[2,2']bifuranyl-5-yl}-11-(2-trimethylsilanyl-ethoxymethoxy)-undec-9-en-1-ol 

Downstream Products

• 193812-14-5 2,4,6-Triisopropyl-benzenesulfonic acid (2R,13R)-2-hydroxy-13-(2-trimethylsilanyl-ethoxymethoxy)-13-{(2R,5R,2'R,5'R)-5'-[(R)-1-(2-trimethylsilanyl-ethoxymethoxy)-undecyl]-octahydro-[2,2']bifuranyl-5-yl}-tridecyl ester 
• 102989-24-2 (+)-asimicin 

Relevant articles and documents

Total synthesis of the Annonaceous acetogenin (+)-asimicin. Development of a new bidirectional strategy

The total synthesis of the Annonaceous acetogenin (+)-asimicin is described. The approach employs the (R)-α-OSEM allylic stannane 7 of >95% ee and the dialdehyde 8 obtained from (S,S)-diethyl tartrate. Addition of 7 to 8 in the presence of InCl3 afforded the bis-adduct 9 in 71% yield. Tosylation and treatment with TBAF led to the core bis-tetrahydrofuran intermediate, diol 11, in 78% yield. Mono tosylation (n-BuLi, TsCl, THF-DMSO) and subsequent hydrogenolysis with LiBEt3H gave alcohol 14. The iodide 15 was coupled with the higher-order vinylcyanocuprate to afford olefin 30. This was converted to diol 31 of high ee by the Sharpless protocol. This diol yielded the epoxide 33 via the mono-trisylate 32. Addition of (R)-lithio-2-(OTBS)-3- butyne in the presence of BF3·OEt2 afforded the alcohol 34. The SEM derivative 35 was treated with TBAF, and the resulting alcohol was converted to the butenolide 38 by a sequence involving treatment with (CF3CO)2O, then Pd(PPh3)4, CO, THF-H2O, and finally AgNO3/silica gel. Cleavage of the SEM protecting group with PPTS in ethanol afforded (+)-asimicin (39).