(2R,6S)-tert-butyl-(2-{6-[(2R)-3-(4-methoxybenzyloxy)-2-methylpropyl]-5,6-dihydro-2H-pyran-2-yl}-ethoxy)-dimethylsilane

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Chemical Name:(2R,6S)-tert-butyl-(2-{6-[(2R)-3-(4-methoxybenzyloxy)-2-methylpropyl]-5,6-dihydro-2H-pyran-2-yl}-ethoxy)-dimethylsilane
CAS No.:445306-73-0
Molecular Formula:C₂₅H₄₂O₄Si
Molecular Weight:434.692
Hs Code.:

Synonyms:(2R,6S)-tert-butyl-(2-{6-[(2R)-3-(4-methoxybenzyloxy)-2-methylpropyl]-5,6-dihydro-2H-pyran-2-yl}-ethoxy)-dimethylsilane

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Chemical Property of (2R,6S)-tert-butyl-(2-{6-[(2R)-3-(4-methoxybenzyloxy)-2-methylpropyl]-5,6-dihydro-2H-pyran-2-yl}-ethoxy)-dimethylsilane

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Technology Process of (2R,6S)-tert-butyl-(2-{6-[(2R)-3-(4-methoxybenzyloxy)-2-methylpropyl]-5,6-dihydro-2H-pyran-2-yl}-ethoxy)-dimethylsilane

There total 27 articles about (2R,6S)-tert-butyl-(2-{6-[(2R)-3-(4-methoxybenzyloxy)-2-methylpropyl]-5,6-dihydro-2H-pyran-2-yl}-ethoxy)-dimethylsilane 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: 90.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 445306-72-9
(2R,6S)-2-{(2R)-6-[3-(4-methoxybenzyloxy)-2-methylpropyl]-5,6-dihydro-2H-pyran-2-yl}-ethanol

: 445306-73-0
(2R,6S)-tert-butyl-(2-{6-[(2R)-3-(4-methoxybenzyloxy)-2-methylpropyl]-5,6-dihydro-2H-pyran-2-yl}-ethoxy)-dimethylsilane

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃;
DOI:10.1016/S0040-4039(02)00472-0

Reference yield:

: 259198-98-6
(4S,6R)-7-(p-methoxybenzyloxy)-6-methylhept-1-en-4-ol

: 445306-73-0
(2R,6S)-tert-butyl-(2-{6-[(2R)-3-(4-methoxybenzyloxy)-2-methylpropyl]-5,6-dihydro-2H-pyran-2-yl}-ethoxy)-dimethylsilane

Guidance literature:: Multi-step reaction with 18 steps

1.1: BH₃ / tetrahydrofuran / 20 °C

1.2: 92 percent / aq. H₂O₂; NaOH / tetrahydrofuran / 20 °C

2.1: 93 percent / imidazole / dimethylformamide / 20 °C

3.1: NaH; 15-crown-5 / tetrahydrofuran / 0.5 h / 0 °C

3.2: 96 percent / tetrahydrofuran / 20 °C

4.1: 93 percent / TBAF / tetrahydrofuran / 20 °C

5.1: 91 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

6.1: 95 percent / oxone / dimethylformamide / 0 °C

7.1: ClCO₂Et; Et₃N / tetrahydrofuran / 0.5 h / 0 °C

7.2: 85 percent / tetrahydrofuran; diethyl ether / 20 °C

8.1: 80 percent / copper(II) hexafluoroacetylacetonate / tetrahydrofuran; CH₂Cl₂ / 4 h / Heating

9.1: 98 percent / NaBH₄ / ethanol / 20 °C

10.1: 97 percent / imidazole / dimethylformamide / 20 °C

11.1: N-methylmorpholine N-oxide; aq. OsO₄ / tetrahydrofuran / 1.5 h / 20 °C

12.1: 240 mg / aq. NaIO₄ / tetrahydrofuran / 20 °C

13.1: 99 percent / NaBH₄ / ethanol / 20 °C

14.1: 97 percent / TBAF / tetrahydrofuran / 20 °C

15.1: 91 percent / imidazole / dimethylformamide / 0.17 h / 20 °C

16.1: 95 percent / Dess-Martin periodinane / CH₂Cl₂ / 20 °C

17.1: lithium hexamethyldisilazide / tetrahydrofuran / 1.5 h / -80 °C

17.2: tetrahydrofuran / 28 h / 0 °C

18.1: 46 mg / Pd(PPh₃)4; LiCl; Bu₃SnH / tetrahydrofuran / 1.5 h / 20 °C

With 1H-imidazole; Oxone; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(II) hexafluoro-2,4-pentanedionate; 15-crown-5; borane; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; chloroformic acid ethyl ester; sodium hydride; Dess-Martin periodane; 4-methylmorpholine N-oxide; triethylamine; lithium chloride; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1248/cpb.53.989

Reference yield:

: 136320-64-4
(2R)-3-[(4-methoxybenzyl)oxy]-2-methylpropanol

: 445306-73-0
(2R,6S)-tert-butyl-(2-{6-[(2R)-3-(4-methoxybenzyloxy)-2-methylpropyl]-5,6-dihydro-2H-pyran-2-yl}-ethoxy)-dimethylsilane

Guidance literature:: Multi-step reaction with 9 steps

1.1: pyridine / ethyl acetate / 16 h / 20 °C

2.1: 11.95 g / dimethylsulfoxide / 20 h / 80 °C

3.1: 80 percent / DIBALH / tetrahydrofuran; hexane / -78 - 20 °C

4.1: (-)-methoxydiisopinocampheylborane / diethyl ether / 3 h / 20 °C

4.2: diethyl ether; pentane / 1 h / -100 °C

4.3: 93 percent / NaBO₃*4H₂O / tetrahydrofuran; H₂O / 2 h / 20 °C

5.1: 84 percent / PPTS / toluene / 2 h / 40 °C / 60004.8 Torr

6.1: 94 percent / Cl₂(PCy₃)2Ru=CHPh / CH₂Cl₂ / 1 h / 40 °C

7.1: montmorillonite K-10 clay / CH₂Cl₂ / 0.5 h / 20 °C

7.2: 86 percent / montmorillonite K₁₀ clay / CH₂Cl₂; H₂O / 1 h / 20 °C

8.1: 99 percent / NaBH₄ / methanol / 0.5 h / 0 °C

9.1: 90 percent / imidazole / CH₂Cl₂; dimethylformamide / 16 h / 20 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; Montmorillonite K-10 clay; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; (-)-B-methoxydiisopinocampheylborane; Grubbs catalyst first generation; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo026743f