4H-Pyran-4-one, 2-[2-[[(1,1-dimethylethyl)diphenylsilyl]oxy]ethyl]tetrahydro-6-(2-propenyl)- , (2S,6S)-

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Chemical Name:4H-Pyran-4-one, 2-[2-[[(1,1-dimethylethyl)diphenylsilyl]oxy]ethyl]tetrahydro-6-(2-propenyl)- , (2S,6S)-
CAS No.:799852-47-4
Molecular Formula:C26H34O3Si
Molecular Weight:422.64
Hs Code.:

Synonyms:

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Chemical Property of 4H-Pyran-4-one, 2-[2-[[(1,1-dimethylethyl)diphenylsilyl]oxy]ethyl]tetrahydro-6-(2-propenyl)- , (2S,6S)-

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Technology Process of 4H-Pyran-4-one, 2-[2-[[(1,1-dimethylethyl)diphenylsilyl]oxy]ethyl]tetrahydro-6-(2-propenyl)- , (2S,6S)-

There total 1 articles about 4H-Pyran-4-one, 2-[2-[[(1,1-dimethylethyl)diphenylsilyl]oxy]ethyl]tetrahydro-6-(2-propenyl)- , (2S,6S)- 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: 86.0%

: 24850-33-7
allyltributylstanane

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

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

Guidance literature:: 2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,3-dihydro-pyran-4-one; With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 ℃; for 0.0833333h;

allyltributylstanane; In dichloromethane; at -78 - -50 ℃; for 3h;

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 0 ℃; for 0.666667h;
DOI:10.1039/b407240e

Reference yield:

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

: (2S,6S)-2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-(2,3-dihydroxy-propyl)-tetrahydro-pyran-4-one

Guidance literature:: With osmium(VIII) oxide; N-methyl-2-indolinone; In tetrahydrofuran; tert-butyl alcohol; at 20 ℃; for 24h;
DOI:10.1039/b407240e

Reference yield:

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

: C₅₂H₆₂N₂O₈Si

Guidance literature:: Multi-step reaction with 18 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

5.1: 99 percent / NaHMDS / tetrahydrofuran / 1 h / -98 °C

6.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

6.2: 86 percent / HMPA / tetrahydrofuran; hexane / 0.5 h / -78 °C

7.1: 91 percent / HF*pyridine / acetonitrile / 5 h / 0 °C

8.1: 93 percent / DMP / CH₂Cl₂ / 0.5 h / 20 °C

9.1: Ba(OH)2*xH₂O / tetrahydrofuran / 0.5 h

9.2: 94 percent / tetrahydrofuran; H₂O / 1.75 h

10.1: 95 percent / Et₃N / diethyl ether / 1 h / 0 °C

11.1: 4 Angstroem molecular sieves / Jacobsen Schiff base hexafluoroantimonate catalyst / acetone / 3 h / 20 °C

11.2: 19 percent / acetone / 40 h / 20 °C

12.1: TBAF; AcOH / tetrahydrofuran / 1 h / 0 °C

13.1: 99 percent / LiAl(O-t-Bu)3H / tetrahydrofuran / 2 h / -78 - -10 °C

14.1: imidazole / dimethylformamide / 27 h / 20 °C

15.1: 24.5 mg / HCl / methanol / 6 h / 20 °C

16.1: 97 percent / aq. LiOH / tetrahydrofuran / 2 h / 20 °C

17.1: Et₃N / CH₂Cl₂ / 0.75 h / 20 °C

18.1: 2.4 mg / DMAP / toluene / 12 h / 20 °C

With 1H-imidazole; lead(IV) acetate; hydrogenchloride; dmap; barium dihydroxide; lithium hydroxide; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; phthalic acid dimethyl ester; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; sodium carbonate; pyridine hydrogenfluoride; acetic acid; phenyllithium; lithium tri-t-butoxyaluminum hydride; triethylamine; triphenylphosphine; [Mn(Sal^tBu)][SbF₆]; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; cyclohexane; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; tert-butyl alcohol; 2.2: Wittig methylenation / 9.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1039/b407240e