(1R,2S,4S,6R,9R,10Z)-2-(tert-butyldiphenylsilanyloxy)-5,12-dioxatricyclo[7.2.1.0(4,6)]-dodec-10-ene

Base Information

Chemical Name:(1R,2S,4S,6R,9R,10Z)-2-(tert-butyldiphenylsilanyloxy)-5,12-dioxatricyclo[7.2.1.0(4,6)]-dodec-10-ene
CAS No.:852213-28-6
Molecular Formula:C₂₆H₃₂O₃Si
Molecular Weight:420.624
Hs Code.:

Synonyms:(1R,2S,4S,6R,9R,10Z)-2-(tert-butyldiphenylsilanyloxy)-5,12-dioxatricyclo[7.2.1.0(4,6)]-dodec-10-ene

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Chemical Property of (1R,2S,4S,6R,9R,10Z)-2-(tert-butyldiphenylsilanyloxy)-5,12-dioxatricyclo[7.2.1.0(4,6)]-dodec-10-ene

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Technology Process of (1R,2S,4S,6R,9R,10Z)-2-(tert-butyldiphenylsilanyloxy)-5,12-dioxatricyclo[7.2.1.0(4,6)]-dodec-10-ene

There total 6 articles about (1R,2S,4S,6R,9R,10Z)-2-(tert-butyldiphenylsilanyloxy)-5,12-dioxatricyclo[7.2.1.0(4,6)]-dodec-10-ene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

: 852213-27-5
(1S,3S,4R,6R,9R)-3-(tert-butyldiphenylsilanyloxy)-4,6-divinyl-5,10-dioxabicyclo[7.1.0]decane

: 852213-28-6
(1R,2S,4S,6R,9R,10Z)-2-(tert-butyldiphenylsilanyloxy)-5,12-dioxatricyclo[7.2.1.0(4,6)]-dodec-10-ene

Guidance literature:: With Grubbs catalyst first generation; In dichloromethane; at 20 ℃; for 20h; Reflux; Inert atmosphere;
DOI:10.1016/j.tetasy.2009.03.010

Reference yield:

: 852213-31-1
(1S,3S,4R,6R,9S)-3-(tert-butyldiphenylsilanyloxy)-4-hydroxymethyl-6-vinyl-5,10-dioxabicyclo[7.1.0]decane

: 852213-28-6
(1R,2S,4S,6R,9R,10Z)-2-(tert-butyldiphenylsilanyloxy)-5,12-dioxatricyclo[7.2.1.0(4,6)]-dodec-10-ene

Guidance literature:: Multi-step reaction with 3 steps

1: 73 percent / o-iodoxybenzoic acid / dimethylsulfoxide / 20 h / 20 °C

2: 98 percent / n-BuLi / tetrahydrofuran / 0.33 h / -78 °C

3: 86 percent / [(PCy₃)2Cl₂Ru(=CHPh)] / CH₂Cl₂ / 18 h / 20 °C

With n-butyllithium; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; Grubbs catalyst first generation; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; 2: Wittig methylenation;
DOI:10.1039/b413426e

Reference yield:

: 852213-25-3
(2R,5Z,8S,9R)-8-(tert-butyldiphenylsilanyloxy)-9-hydroxymethyl-2-vinyl-2,3,4,7,8,9-hexahydrooxonine

: 852213-28-6
(1R,2S,4S,6R,9R,10Z)-2-(tert-butyldiphenylsilanyloxy)-5,12-dioxatricyclo[7.2.1.0(4,6)]-dodec-10-ene

Guidance literature:: Multi-step reaction with 4 steps

1: 63 percent / mCPBA / tetrahydrofuran / 0 - 20 °C

2: 73 percent / o-iodoxybenzoic acid / dimethylsulfoxide / 20 h / 20 °C

3: 98 percent / n-BuLi / tetrahydrofuran / 0.33 h / -78 °C

4: 86 percent / [(PCy₃)2Cl₂Ru(=CHPh)] / CH₂Cl₂ / 18 h / 20 °C

With n-butyllithium; 3-chloro-benzenecarboperoxoic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; Grubbs catalyst first generation; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; 3: Wittig methylenation;
DOI:10.1039/b413426e