tert-Butyl-{2-[(2R,6S)-6-(3,3-dibromo-allyl)-4-methylene-tetrahydro-pyran-2-yl]-ethoxy}-diphenyl-silane

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Chemical Name:tert-Butyl-{2-[(2R,6S)-6-(3,3-dibromo-allyl)-4-methylene-tetrahydro-pyran-2-yl]-ethoxy}-diphenyl-silane
CAS No.:799852-50-9
Molecular Formula:C₂₇H₃₄Br₂O₂Si
Molecular Weight:578.459
Hs Code.:

Synonyms:tert-Butyl-{2-[(2R,6S)-6-(3,3-dibromo-allyl)-4-methylene-tetrahydro-pyran-2-yl]-ethoxy}-diphenyl-silane

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Chemical Property of tert-Butyl-{2-[(2R,6S)-6-(3,3-dibromo-allyl)-4-methylene-tetrahydro-pyran-2-yl]-ethoxy}-diphenyl-silane

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Technology Process of tert-Butyl-{2-[(2R,6S)-6-(3,3-dibromo-allyl)-4-methylene-tetrahydro-pyran-2-yl]-ethoxy}-diphenyl-silane

There total 2 articles about tert-Butyl-{2-[(2R,6S)-6-(3,3-dibromo-allyl)-4-methylene-tetrahydro-pyran-2-yl]-ethoxy}-diphenyl-silane 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:

: 799852-47-4
(2S,6S)-2-Allyl-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-tetrahydro-pyran-4-one

: 799852-50-9
tert-Butyl-{2-[(2R,6S)-6-(3,3-dibromo-allyl)-4-methylene-tetrahydro-pyran-2-yl]-ethoxy}-diphenyl-silane

Guidance literature:: Multi-step reaction with 4 steps

1.1: 8.38 g / aq. NMO; OsO₄ / tetrahydrofuran; 2-methyl-propan-2-ol / 24 h / 20 °C

2.1: PhLi / tetrahydrofuran; cyclohexane; diethyl ether / 2 h / 0 °C

2.2: 7.61 g / tetrahydrofuran; cyclohexane; diethyl ether / 3 h / -40 - -20 °C

3.1: 5.73 g / Na₂CO₃; Pb(OAc)4 / CH₂Cl₂ / 1.5 h / 0 - 20 °C

4.1: PPh₃ / CH₂Cl₂ / 0.17 h / -10 °C

4.2: 98 percent / CH₂Cl₂ / 0.5 h / -10 °C

With lead(IV) acetate; osmium(VIII) oxide; N-methyl-2-indolinone; sodium carbonate; phenyllithium; triphenylphosphine; In tetrahydrofuran; diethyl ether; dichloromethane; cyclohexane; tert-butyl alcohol; 2.2: Wittig methylenation;
DOI:10.1039/b407240e

Reference yield:

: 288092-41-1
2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,3-dihydro-pyran-4-one

: 799852-50-9
tert-Butyl-{2-[(2R,6S)-6-(3,3-dibromo-allyl)-4-methylene-tetrahydro-pyran-2-yl]-ethoxy}-diphenyl-silane

Guidance literature:: Multi-step reaction with 5 steps

1.1: TMSOTf / CH₂Cl₂ / 0.08 h / -78 °C

1.2: CH₂Cl₂ / 3 h / -78 - -50 °C

1.3: 86 percent / TBAF; AcOH / tetrahydrofuran / 0.67 h / 0 °C

2.1: 8.38 g / aq. NMO; OsO₄ / tetrahydrofuran; 2-methyl-propan-2-ol / 24 h / 20 °C

3.1: PhLi / tetrahydrofuran; cyclohexane; diethyl ether / 2 h / 0 °C

3.2: 7.61 g / tetrahydrofuran; cyclohexane; diethyl ether / 3 h / -40 - -20 °C

4.1: 5.73 g / Na₂CO₃; Pb(OAc)4 / CH₂Cl₂ / 1.5 h / 0 - 20 °C

5.1: PPh₃ / CH₂Cl₂ / 0.17 h / -10 °C

5.2: 98 percent / CH₂Cl₂ / 0.5 h / -10 °C

With lead(IV) acetate; osmium(VIII) oxide; N-methyl-2-indolinone; trimethylsilyl trifluoromethanesulfonate; sodium carbonate; phenyllithium; triphenylphosphine; In tetrahydrofuran; diethyl ether; dichloromethane; cyclohexane; tert-butyl alcohol; 3.2: Wittig methylenation;
DOI:10.1039/b407240e