(Z)-(S)-6-((4S,5S)-2,2-Dimethyl-5-prop-2-ynyl-[1,3]dioxolan-4-yl)-6-(4-methoxy-benzyloxy)-hex-4-en-2-ol

Base Information

Chemical Name:(Z)-(S)-6-((4S,5S)-2,2-Dimethyl-5-prop-2-ynyl-[1,3]dioxolan-4-yl)-6-(4-methoxy-benzyloxy)-hex-4-en-2-ol
CAS No.:460348-30-5
Molecular Formula:C₂₂H₃₀O₅
Molecular Weight:374.477
Hs Code.:

Synonyms:(Z)-(S)-6-((4S,5S)-2,2-Dimethyl-5-prop-2-ynyl-[1,3]dioxolan-4-yl)-6-(4-methoxy-benzyloxy)-hex-4-en-2-ol

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Chemical Property of (Z)-(S)-6-((4S,5S)-2,2-Dimethyl-5-prop-2-ynyl-[1,3]dioxolan-4-yl)-6-(4-methoxy-benzyloxy)-hex-4-en-2-ol

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Technology Process of (Z)-(S)-6-((4S,5S)-2,2-Dimethyl-5-prop-2-ynyl-[1,3]dioxolan-4-yl)-6-(4-methoxy-benzyloxy)-hex-4-en-2-ol

There total 10 articles about (Z)-(S)-6-((4S,5S)-2,2-Dimethyl-5-prop-2-ynyl-[1,3]dioxolan-4-yl)-6-(4-methoxy-benzyloxy)-hex-4-en-2-ol 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: 97.0%

: 460348-27-0
tert-Butyl-[(Z)-(S)-5-((4S,5S)-2,2-dimethyl-5-prop-2-ynyl-[1,3]dioxolan-4-yl)-5-(4-methoxy-benzyloxy)-1-methyl-pent-3-enyloxy]-dimethyl-silane

: 460348-30-5
(Z)-(S)-6-((4S,5S)-2,2-Dimethyl-5-prop-2-ynyl-[1,3]dioxolan-4-yl)-6-(4-methoxy-benzyloxy)-hex-4-en-2-ol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 10h;
DOI:10.1016/S0040-4039(02)00870-5

Reference yield:

: 103712-19-2
(S)-(+)-5-(trimethylsilyl)-4-pentyn-2-ol

: 460348-30-5
(Z)-(S)-6-((4S,5S)-2,2-Dimethyl-5-prop-2-ynyl-[1,3]dioxolan-4-yl)-6-(4-methoxy-benzyloxy)-hex-4-en-2-ol

Guidance literature:: Multi-step reaction with 6 steps

1.1: imidazole / dimethylformamide / 20 °C

1.2: 86 percent / K₂CO₃ / methanol / 5 h / 20 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C

2.2: 86 percent / I₂ / tetrahydrofuran

3.1: SiaBH / tetrahydrofuran / 3 h / -20 - 0 °C

3.2: 89 percent / AcOH / 3 h / 65 °C

4.1: t-BuLi / diethyl ether; pentane / 0.25 h / -78 °C

4.2: 56 percent / diethyl ether; pentane / -78 - 0 °C

5.1: K₂CO₃ / methanol / 5 h / 20 °C

5.2: 72 percent / CF₃SO₃H / diethyl ether / 4 h / 20 °C

6.1: 97 percent / TBAF / tetrahydrofuran / 10 h / 20 °C

With 1H-imidazole; n-butyllithium; tetrabutyl ammonium fluoride; tert.-butyl lithium; bis-(1,2-dimethylpropyl)borane; potassium carbonate; In tetrahydrofuran; methanol; diethyl ether; hexane; N,N-dimethyl-formamide; pentane;
DOI:10.1016/S0040-4039(02)00870-5

Reference yield:

: 150406-35-2
(S)-tert-butyldimethyl(pent-4-yn-2-yloxy)silane

: 460348-30-5
(Z)-(S)-6-((4S,5S)-2,2-Dimethyl-5-prop-2-ynyl-[1,3]dioxolan-4-yl)-6-(4-methoxy-benzyloxy)-hex-4-en-2-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C

1.2: 86 percent / I₂ / tetrahydrofuran

2.1: SiaBH / tetrahydrofuran / 3 h / -20 - 0 °C

2.2: 89 percent / AcOH / 3 h / 65 °C

3.1: t-BuLi / diethyl ether; pentane / 0.25 h / -78 °C

3.2: 56 percent / diethyl ether; pentane / -78 - 0 °C

4.1: K₂CO₃ / methanol / 5 h / 20 °C

4.2: 72 percent / CF₃SO₃H / diethyl ether / 4 h / 20 °C

5.1: 97 percent / TBAF / tetrahydrofuran / 10 h / 20 °C

With n-butyllithium; tetrabutyl ammonium fluoride; tert.-butyl lithium; bis-(1,2-dimethylpropyl)borane; potassium carbonate; In tetrahydrofuran; methanol; diethyl ether; hexane; pentane;
DOI:10.1016/S0040-4039(02)00870-5