8-ethynyl-2-(tert-butyldiphenylsilyloxymethyl)-1,7-dioxaspiro[5.5]undecane

Base Information

Chemical Name:8-ethynyl-2-(tert-butyldiphenylsilyloxymethyl)-1,7-dioxaspiro[5.5]undecane
CAS No.:1392104-15-2
Molecular Formula:C₂₈H₃₆O₃Si
Molecular Weight:448.678
Hs Code.:

Synonyms:8-ethynyl-2-(tert-butyldiphenylsilyloxymethyl)-1,7-dioxaspiro[5.5]undecane

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Chemical Property of 8-ethynyl-2-(tert-butyldiphenylsilyloxymethyl)-1,7-dioxaspiro[5.5]undecane

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Technology Process of 8-ethynyl-2-(tert-butyldiphenylsilyloxymethyl)-1,7-dioxaspiro[5.5]undecane

There total 10 articles about 8-ethynyl-2-(tert-butyldiphenylsilyloxymethyl)-1,7-dioxaspiro[5.5]undecane 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: 75.0%

: 1392104-11-8
(3S,11S)-11-(tert-butyldimethylsilyloxy)-12-(tert-butyldiphenylsilyloxy)-7-(1,3-dioxolan-2-yl)dodec-1-yn-3-ol

: 1392104-15-2
8-ethynyl-2-(tert-butyldiphenylsilyloxymethyl)-1,7-dioxaspiro[5.5]undecane

Guidance literature:: With camphor-10-sulfonic acid; In ethanol; water; at 20 ℃; for 3h;
DOI:10.1039/c2ob06802h

Reference yield:

: 11(S)-(tert-butyldimethylsilyloxy)-12-(tert-butyldiphenylsilyloxy)-7-(1,3-dioxolan-2-yl)dodec-1-yn-⁽³⁾-ol

: 1392104-15-2
8-ethynyl-2-(tert-butyldiphenylsilyloxymethyl)-1,7-dioxaspiro[5.5]undecane

Guidance literature:: Multi-step reaction with 3 steps

1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 2.5 h / 20 - 40 °C

2: borane Ν,Ν-diethylaniline complex; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 2.5 h / 0 °C / Inert atmosphere

3: camphor-10-sulfonic acid / ethanol; water / 3 h / 20 °C

With borane Ν,Ν-diethylaniline complex; camphor-10-sulfonic acid; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; ethanol; water; dimethyl sulfoxide;
DOI:10.1039/c2ob06802h

Reference yield:

: 1392104-16-3
6-(tert-butyldiphenylsilyloxy)-(5S)-5-hydroxyl-N-methoxy-N-methylhexanamide

: 1392104-15-2
8-ethynyl-2-(tert-butyldiphenylsilyloxymethyl)-1,7-dioxaspiro[5.5]undecane

Guidance literature:: Multi-step reaction with 6 steps

1.1: 1H-imidazole; dmap / dichloromethane / 13 h / 20 - 45 °C / Inert atmosphere

2.1: iodine; magnesium / diethyl ether / Inert atmosphere

2.2: 3 h / 0 °C / Inert atmosphere

3.1: bismuth(lll) trifluoromethanesulfonate; orthoformic acid triethyl ester / toluene / 20 °C

4.1: sodium hydrogencarbonate; ozone; Sudan III / dichloromethane / 1 h / -78 °C / Inert atmosphere

4.2: 0.5 h / -78 - 20 °C / Inert atmosphere

5.1: tetrahydrofuran / 3 h / 0 °C / Inert atmosphere

6.1: camphor-10-sulfonic acid / ethanol; water / 3 h / 20 °C

With bismuth(lll) trifluoromethanesulfonate; 1H-imidazole; dmap; camphor-10-sulfonic acid; iodine; sodium hydrogencarbonate; ozone; magnesium; orthoformic acid triethyl ester; Sudan III; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; toluene;
DOI:10.1039/c2ob06802h