(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

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Chemical Name:(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
CAS No.:302554-90-1
Molecular Formula:C₃₅H₄₄O₅Si
Molecular Weight:572.817
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 24 articles about (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 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: 96.0%

: 218898-32-9
(2S)-4-methyl-3,6-dihydro-2H-pyran-2-carbaldehyde

: 302554-84-3
dimethyl (3S)-3-(tert-butyldiphenylsilyloxy)-2-oxo-7-[(2R,S)-tetrahydro-2H-pyran-2-yloxy]-hept-5-ynyl-phosphonate

: 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

Guidance literature:: With triethylamine; lithium chloride; In tetrahydrofuran; at 0 - 20 ℃;
DOI:10.1021/jo026743f

Reference yield:

: 387392-14-5
(1S)-1-{(4R,5R)-5-[(1S)-1-hydroxy-3-methyl-3-butenyl]-2,2-dimethyl-1,3-dioxolan-4-yl}-3-methyl-3-buten-1-ol

: 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

Guidance literature:: Multi-step reaction with 5 steps

1: 100 percent / KOtBu / 13 / 20 °C

2: 83 percent / [P(C₆H₁₁)3]2Cl₂Ru=CHPh / CH₂Cl₂ / 5 h / 20 °C

3: 93 percent / TFA / CH₂Cl₂ / 3.5 h / 0 °C

4: Pb(OAc)4; Na₂CO₃ / CH₂Cl₂ / 0.25 h / 0 °C

5: 96 percent / LiCl; Et₃N / tetrahydrofuran / 0 - 20 °C

With lead(IV) acetate; potassium tert-butylate; sodium carbonate; triethylamine; trifluoroacetic acid; lithium chloride; Grubbs catalyst first generation; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo026743f

Reference yield:

: 385809-17-6
(4S,5S)-4,5-bis-1-[(S)-allyloxy-3-methylbut-3-enyl]-2,2-dimethyl-[1,3]-dioxolane

: 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

Guidance literature:: Multi-step reaction with 4 steps

1: 83 percent / [P(C₆H₁₁)3]2Cl₂Ru=CHPh / CH₂Cl₂ / 5 h / 20 °C

2: 93 percent / TFA / CH₂Cl₂ / 3.5 h / 0 °C

3: Pb(OAc)4; Na₂CO₃ / CH₂Cl₂ / 0.25 h / 0 °C

4: 96 percent / LiCl; Et₃N / tetrahydrofuran / 0 - 20 °C

With lead(IV) acetate; sodium carbonate; triethylamine; trifluoroacetic acid; lithium chloride; Grubbs catalyst first generation; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo026743f