(E)-1-((2R,5S,6S)-6-(2-(tert-butyldiphenylsilyloxy)ethyl)-5-methyltetrahydro-2H-pyran-2-yl)pent-3-en-2-one

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Chemical Name:(E)-1-((2R,5S,6S)-6-(2-(tert-butyldiphenylsilyloxy)ethyl)-5-methyltetrahydro-2H-pyran-2-yl)pent-3-en-2-one
CAS No.:862736-26-3
Molecular Formula:C₂₉H₄₀O₃Si
Molecular Weight:464.72
Hs Code.:

Synonyms:(E)-1-((2R,5S,6S)-6-(2-(tert-butyldiphenylsilyloxy)ethyl)-5-methyltetrahydro-2H-pyran-2-yl)pent-3-en-2-one

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Chemical Property of (E)-1-((2R,5S,6S)-6-(2-(tert-butyldiphenylsilyloxy)ethyl)-5-methyltetrahydro-2H-pyran-2-yl)pent-3-en-2-one

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Technology Process of (E)-1-((2R,5S,6S)-6-(2-(tert-butyldiphenylsilyloxy)ethyl)-5-methyltetrahydro-2H-pyran-2-yl)pent-3-en-2-one

There total 9 articles about (E)-1-((2R,5S,6S)-6-(2-(tert-butyldiphenylsilyloxy)ethyl)-5-methyltetrahydro-2H-pyran-2-yl)pent-3-en-2-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: 70.0%

: 862735-91-9
tert-butyl (2-((2S,3S,6R)-3-methyl-6-((2-((E)-prop-1-enyl)-1,3-dithian-2-yl)methyl)tetrahydro-2H-pyran-2-yl)ethoxy)diphenylsilane

: 862736-26-3
(E)-1-((2R,5S,6S)-6-(2-(tert-butyldiphenylsilyloxy)ethyl)-5-methyltetrahydro-2H-pyran-2-yl)pent-3-en-2-one

Guidance literature:: With periodic acid; In tetrahydrofuran; at 0 ℃; for 0.0833333h;
DOI:10.1021/ol050982i

Reference yield:

: 862736-01-4
(Z)-(2S,3S)-3-(dimethyl-phenyl-silanyl)-2-hydroxy-hex-4-enoic acid methyl ester

: 862736-26-3
(E)-1-((2R,5S,6S)-6-(2-(tert-butyldiphenylsilyloxy)ethyl)-5-methyltetrahydro-2H-pyran-2-yl)pent-3-en-2-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

2.1: 66 percent / triflic acid; TMSOTf / CH₂Cl₂ / 24 h / -50 °C

3.1: 93 percent / H₂ / PtO₂ / methanol / 12 h / 20 °C

4.1: 88 percent / imidazole; DMAP / dimethylformamide / 0 - 20 °C

5.1: 90 percent / LiBH₄ / diethyl ether / 2 h / 20 °C

6.1: 91 percent / 2,6-lutidine; methyltriphenoxyphosphonium iodide / dimethylformamide / 1 h

7.1: tert-butyllithium; HMPA / tetrahydrofuran; pentane / 1 h / -78 °C

7.2: 95 percent / tetrahydrofuran; pentane / -78 - 0 °C

8.1: 70 percent / H₅IO₆ / tetrahydrofuran / 0.08 h / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium borohydride; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; methyltriphenoxyphosphonium iodide; hydrogen; tert.-butyl lithium; periodic acid; platinum(IV) oxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; pentane;
DOI:10.1021/ol050982i

Reference yield:

: (2R,5S)-6-(2-benzyloxy-ethyl)-5-methyl-5,6-dihydro-2H-pyran-2-carboxylic acid methyl ester

: 862736-26-3
(E)-1-((2R,5S,6S)-6-(2-(tert-butyldiphenylsilyloxy)ethyl)-5-methyltetrahydro-2H-pyran-2-yl)pent-3-en-2-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: 93 percent / H₂ / PtO₂ / methanol / 12 h / 20 °C

2.1: 88 percent / imidazole; DMAP / dimethylformamide / 0 - 20 °C

3.1: 90 percent / LiBH₄ / diethyl ether / 2 h / 20 °C

4.1: 91 percent / 2,6-lutidine; methyltriphenoxyphosphonium iodide / dimethylformamide / 1 h

5.1: tert-butyllithium; HMPA / tetrahydrofuran; pentane / 1 h / -78 °C

5.2: 95 percent / tetrahydrofuran; pentane / -78 - 0 °C

6.1: 70 percent / H₅IO₆ / tetrahydrofuran / 0.08 h / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium borohydride; methyltriphenoxyphosphonium iodide; hydrogen; tert.-butyl lithium; periodic acid; platinum(IV) oxide; In tetrahydrofuran; methanol; diethyl ether; N,N-dimethyl-formamide; pentane;
DOI:10.1021/ol050982i