(1E,3S,4S)-4-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)-1-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-8-[(2R,S)-tetrahydro-2H-pyran-2-yloxy]oct-1-en-6-yne

Base Information

Chemical Name:(1E,3S,4S)-4-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)-1-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-8-[(2R,S)-tetrahydro-2H-pyran-2-yloxy]oct-1-en-6-yne
CAS No.:302554-98-9
Molecular Formula:C₃₇H₅₀O₆Si
Molecular Weight:618.886
Hs Code.:

(1E,3S,4S)-4-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)-1-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-8-[(2R,S)-tetrahydro-2H-pyran-2-yloxy]oct-1-en-6-yne

Synonyms:(1E,3S,4S)-4-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)-1-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-8-[(2R,S)-tetrahydro-2H-pyran-2-yloxy]oct-1-en-6-yne

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Chemical Property of (1E,3S,4S)-4-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)-1-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-8-[(2R,S)-tetrahydro-2H-pyran-2-yloxy]oct-1-en-6-yne

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Technology Process of (1E,3S,4S)-4-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)-1-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-8-[(2R,S)-tetrahydro-2H-pyran-2-yloxy]oct-1-en-6-yne

There total 27 articles about (1E,3S,4S)-4-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)-1-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-8-[(2R,S)-tetrahydro-2H-pyran-2-yloxy]oct-1-en-6-yne 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%

: 107-30-2
chloromethyl methyl ether

: 302554-91-2
(1E,3S,4S)-4-(tert-butyldiphenylsilyloxy)-1-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-8-[(2R,S)-tetrahydro-2H-pyran-2-yloxy]oct-1-en-6-yn-3-ol

: 302554-98-9
(1E,3S,4S)-4-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)-1-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-8-[(2R,S)-tetrahydro-2H-pyran-2-yloxy]oct-1-en-6-yne

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; for 3h;
DOI:10.1016/S0040-4039(00)00961-8

Reference yield: 60.0%

: 107-30-2
chloromethyl methyl ether

: 302554-90-1
(1E,4S)-4-(tert-butyldiphenylsilyloxy)-1-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-8-[(2R,S)-tetrahydro-2H-pyran-2-yloxy]oct-1-en-6-yn-3-one

: 302554-98-9
(1E,3S,4S)-4-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)-1-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-8-[(2R,S)-tetrahydro-2H-pyran-2-yloxy]oct-1-en-6-yne

Guidance literature:: (1E,4S)-4-(tert-butyldiphenylsilyloxy)-1-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-8-[(2R,S)-tetrahydro-2H-pyran-2-yloxy]oct-1-en-6-yn-3-one; With sodium tetrahydroborate; cerium(III) chloride; In methanol;

chloromethyl methyl ether; With tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine; Further stages.;
DOI:10.1002/1615-4169(200208)344:6/7<573::AID-ADSC573>3.0.CO;2-C

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 302554-98-9
(1E,3S,4S)-4-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)-1-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-8-[(2R,S)-tetrahydro-2H-pyran-2-yloxy]oct-1-en-6-yne

Guidance literature:: Multi-step reaction with 10 steps

1.1: 81 percent / imidazole / dimethylformamide / 4 h / 20 °C

2.1: 91 percent / DIBALH / CH₂Cl₂; heptane / -78 - 20 °C

3.1: 78 percent / TsOH / 0.33 h / 20 °C

4.1: 97 percent / DDQ / CH₂Cl₂; H₂O / 1 h / 20 °C

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

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

7.1: 1.71 g / diethyl ether

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

8.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C

9.1: 96 percent / LiCl; Et₃N / tetrahydrofuran / 0 - 20 °C

10.1: NaBH₄; CeCl₃ / methanol / 0.08 h

10.2: 51 mg / iPr₂NEt / dimethylformamide / 3.5 h / 0 - 20 °C

With 1H-imidazole; 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; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; In tetrahydrofuran; methanol; diethyl ether; hexane; n-heptane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; tert-butyl alcohol; 6.1: Pinnick oxidation;
DOI:10.1021/jo026743f