2-<3α,5α-bis-<(tert-butyldiphenylsilyl)oxy>-2β-<<(3S)-(tert-butyldiphenylsilyl)oxy>-(E,Z)-1,5-undecadien>-1β-cyclopentane>ethan-1-al

Base Information

Chemical Name:2-<3α,5α-bis-<(tert-butyldiphenylsilyl)oxy>-2β-<<(3S)-(tert-butyldiphenylsilyl)oxy>-(E,Z)-1,5-undecadien>-1β-cyclopentane>ethan-1-al
CAS No.:219308-81-3
Molecular Formula:C₆₆H₈₄O₄Si₃
Molecular Weight:1025.65
Hs Code.:

Synonyms:2-<3α,5α-bis-<(tert-butyldiphenylsilyl)oxy>-2β-<<(3S)-(tert-butyldiphenylsilyl)oxy>-(E,Z)-1,5-undecadien>-1β-cyclopentane>ethan-1-al

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Chemical Property of 2-<3α,5α-bis-<(tert-butyldiphenylsilyl)oxy>-2β-<<(3S)-(tert-butyldiphenylsilyl)oxy>-(E,Z)-1,5-undecadien>-1β-cyclopentane>ethan-1-al

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Technology Process of 2-<3α,5α-bis-<(tert-butyldiphenylsilyl)oxy>-2β-<<(3S)-(tert-butyldiphenylsilyl)oxy>-(E,Z)-1,5-undecadien>-1β-cyclopentane>ethan-1-al

There total 14 articles about 2-<3α,5α-bis-<(tert-butyldiphenylsilyl)oxy>-2β-<<(3S)-(tert-butyldiphenylsilyl)oxy>-(E,Z)-1,5-undecadien>-1β-cyclopentane>ethan-1-al 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: 95.0%

: 219309-18-9
2-<3α,5α-bis-<(tert-butyldiphenylsilyl)oxy>-2β-<<(3S)-(tert-butyldiphenylsilyl)oxy>-(E,Z)-1,5-undecadien>-1β-cyclopentane>ethan-1-ol

: 219308-81-3
2-<3α,5α-bis-<(tert-butyldiphenylsilyl)oxy>-2β-<<(3S)-(tert-butyldiphenylsilyl)oxy>-(E,Z)-1,5-undecadien>-1β-cyclopentane>ethan-1-al

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at 0 ℃; for 4h;
DOI:10.1021/ja982596k

Reference yield:

: 59995-47-0,61305-27-9,61740-29-2,59995-49-2
(S)-4-hydroxycyclopent-2-en-1-one

: 219308-81-3
2-<3α,5α-bis-<(tert-butyldiphenylsilyl)oxy>-2β-<<(3S)-(tert-butyldiphenylsilyl)oxy>-(E,Z)-1,5-undecadien>-1β-cyclopentane>ethan-1-al

Guidance literature:: Multi-step reaction with 13 steps

1: 60 percent / Et₃N, DMAP / CH₂Cl₂ / Ambient temperature

2: 1.) BHT, 2.) pyridinium p-toluenosulfonate / 1.) xylene, 140 deg C, 10 h, 2.) methanol, RT, 2 h

3: NaBH₄ / methanol / 3 h / -78 °C

4: 85 percent / imidazole / dimethylformamide / 2 h / Ambient temperature

5: 92 percent / p-TsOH / acetone / 0.67 h / Ambient temperature

6: 95 percent / trimethylamine oxide dihydrate, OsO₄, t-BuOH / acetonitrile / 1 h / Ambient temperature

7: NaIO₄ / methanol; H₂O / 20 h / Ambient temperature

8: diisopropylethylamine / acetonitrile; diethyl ether / 24 h

9: 1.) sodium hexamethyldisilazide / 1.) THF, -78 deg C, 30 min, 2.) THF, 0 deg C, 12 h

10: 85 percent / (S)-BINAL-H / tetrahydrofuran / 4 h / -100 - -78 °C

11: 90 percent / imidazole / dimethylformamide / 2 h / Ambient temperature

12: 92 percent / DIBAL-H / toluene / 4 h / -78 °C

13: 95 percent / oxalyl chloride, dimethyl sulfoxide, Et₃N / CH₂Cl₂ / 4 h / 0 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; oxalyl dichloride; trimethylamine-N-oxide; 2,6-di-tert-butyl-4-methyl-phenol; (-)-(S)-BINAL-H; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; tert-butyl alcohol; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;
DOI:10.1021/ja982596k

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 219308-81-3
2-<3α,5α-bis-<(tert-butyldiphenylsilyl)oxy>-2β-<<(3S)-(tert-butyldiphenylsilyl)oxy>-(E,Z)-1,5-undecadien>-1β-cyclopentane>ethan-1-al

Guidance literature:: Multi-step reaction with 13 steps

1: 60 percent / Et₃N, DMAP / CH₂Cl₂ / Ambient temperature

2: 1.) BHT, 2.) pyridinium p-toluenosulfonate / 1.) xylene, 140 deg C, 10 h, 2.) methanol, RT, 2 h

3: NaBH₄ / methanol / 3 h / -78 °C

4: 85 percent / imidazole / dimethylformamide / 2 h / Ambient temperature

5: 92 percent / p-TsOH / acetone / 0.67 h / Ambient temperature

6: 95 percent / trimethylamine oxide dihydrate, OsO₄, t-BuOH / acetonitrile / 1 h / Ambient temperature

7: NaIO₄ / methanol; H₂O / 20 h / Ambient temperature

8: diisopropylethylamine / acetonitrile; diethyl ether / 24 h

9: 1.) sodium hexamethyldisilazide / 1.) THF, -78 deg C, 30 min, 2.) THF, 0 deg C, 12 h

10: 85 percent / (S)-BINAL-H / tetrahydrofuran / 4 h / -100 - -78 °C

11: 90 percent / imidazole / dimethylformamide / 2 h / Ambient temperature

12: 92 percent / DIBAL-H / toluene / 4 h / -78 °C

13: 95 percent / oxalyl chloride, dimethyl sulfoxide, Et₃N / CH₂Cl₂ / 4 h / 0 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; oxalyl dichloride; trimethylamine-N-oxide; 2,6-di-tert-butyl-4-methyl-phenol; (-)-(S)-BINAL-H; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; tert-butyl alcohol; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;
DOI:10.1021/ja982596k