ethyl (5S)-5-(tert-butyldiphenylsilyloxy)-6-(4-methoxybenzyloxy)hex-2-ynoate

Base Information

Chemical Name:ethyl (5S)-5-(tert-butyldiphenylsilyloxy)-6-(4-methoxybenzyloxy)hex-2-ynoate
CAS No.:302554-95-6
Molecular Formula:C₃₂H₃₈O₅Si
Molecular Weight:530.736
Hs Code.:

Synonyms:ethyl (5S)-5-(tert-butyldiphenylsilyloxy)-6-(4-methoxybenzyloxy)hex-2-ynoate

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Chemical Property of ethyl (5S)-5-(tert-butyldiphenylsilyloxy)-6-(4-methoxybenzyloxy)hex-2-ynoate

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Technology Process of ethyl (5S)-5-(tert-butyldiphenylsilyloxy)-6-(4-methoxybenzyloxy)hex-2-ynoate

There total 1 articles about ethyl (5S)-5-(tert-butyldiphenylsilyloxy)-6-(4-methoxybenzyloxy)hex-2-ynoate 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: 100.0%

: 58479-61-1
tert-butylchlorodiphenylsilane

: 302554-85-4
ethyl (5S)-5-hydroxy-6-(4-methoxybenzyloxy)hex-2-ynoate

: 302554-95-6
ethyl (5S)-5-(tert-butyldiphenylsilyloxy)-6-(4-methoxybenzyloxy)hex-2-ynoate

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; for 5h;
DOI:10.1016/S0040-4039(00)00961-8

Reference yield: 91.0%

: 302554-95-6
ethyl (5S)-5-(tert-butyldiphenylsilyloxy)-6-(4-methoxybenzyloxy)hex-2-ynoate

: 302554-96-7
(5S)-5-(tert-butyldiphenylsilyloxy)-6-(4-methoxybenzyloxy)hex-2-yn-1-ol

Guidance literature:: With diisobutylaluminium hydride; In dichloromethane; at 78 ℃; for 1h;
DOI:10.1016/S0040-4039(00)00961-8

Reference yield:

: 302554-95-6
ethyl (5S)-5-(tert-butyldiphenylsilyloxy)-6-(4-methoxybenzyloxy)hex-2-ynoate

: ((2S,3S)-3-{(2R,3R,4E)-2-{[tert-butyl(diphenyl)silyl]oxy}-3-(methoxymethoxy)-5-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]pent-4-enyl}oxiran-2-yl)methanol

Guidance literature:: Multi-step reaction with 12 steps

1.1: 91 percent / DIBALH / CH₂Cl₂; heptane / -78 - 20 °C

2.1: 78 percent / TsOH / 0.33 h / 20 °C

3.1: 97 percent / DDQ / CH₂Cl₂; H₂O / 1 h / 20 °C

4.1: SO₃*pyridine; Et₃N / dimethylsulfoxide; CH₂Cl₂ / 0.5 h / 0 °C

5.1: NaClO₂; aq. K₂HPO₄; 2,3-dimethylbut-2-ene / 2-methyl-propan-2-ol / 2 h / 0 °C

6.1: 1.71 g / diethyl ether

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

7.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C

8.1: 96 percent / LiCl; Et₃N / tetrahydrofuran / 0 - 20 °C

9.1: NaBH₄; CeCl₃ / methanol / 0.08 h

9.2: 51 mg / iPr₂NEt / dimethylformamide / 3.5 h / 0 - 20 °C

10.1: 89 percent / aq. HCl / methanol / 0.67 h / 0 - 20 °C

11.1: 70 percent / Red-Al(R) / diethyl ether; toluene / 20 °C

12.1: Ti(OiPr)4; t-BuO₂H; (+)-diethyl tartrate / 4 Angstroem molecular sieves / CH₂Cl₂ / 24 h / -20 °C

With titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; sodium chlorite; sodium tetrahydroborate; dipotassium hydrogenphosphate; n-butyllithium; cerium(III) chloride; 2,3-Dimethyl-2-butene; pyridine-SO₃ complex; diisobutylaluminium hydride; toluene-4-sulfonic acid; (+)-Weinsaeure-diethylester; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; 4 A molecular sieve; In tetrahydrofuran; methanol; diethyl ether; hexane; n-heptane; dichloromethane; water; dimethyl sulfoxide; toluene; tert-butyl alcohol; 5.1: Pinnick oxidation / 12.1: Sharpless epoxidation;
DOI:10.1021/jo026743f