((2S,3S,4S)-1-(4-methoxybenzyloxy)-6-iodo-2,4-dimethylhex-5-yn-3-yloxy)(tert-butyl)dimethylsilane

Base Information

Chemical Name:((2S,3S,4S)-1-(4-methoxybenzyloxy)-6-iodo-2,4-dimethylhex-5-yn-3-yloxy)(tert-butyl)dimethylsilane
CAS No.:945402-31-3
Molecular Formula:C₂₂H₃₅IO₃Si
Molecular Weight:502.508
Hs Code.:

Synonyms:((2S,3S,4S)-1-(4-methoxybenzyloxy)-6-iodo-2,4-dimethylhex-5-yn-3-yloxy)(tert-butyl)dimethylsilane

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Chemical Property of ((2S,3S,4S)-1-(4-methoxybenzyloxy)-6-iodo-2,4-dimethylhex-5-yn-3-yloxy)(tert-butyl)dimethylsilane

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Technology Process of ((2S,3S,4S)-1-(4-methoxybenzyloxy)-6-iodo-2,4-dimethylhex-5-yn-3-yloxy)(tert-butyl)dimethylsilane

There total 7 articles about ((2S,3S,4S)-1-(4-methoxybenzyloxy)-6-iodo-2,4-dimethylhex-5-yn-3-yloxy)(tert-butyl)dimethylsilane 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: 99.0%

: 945402-07-3
(+)-tert-butyl(((2S,3S,4S)-1-((4-methoxybenzyl)oxy)-2,4-dimethylhex-5-yn-3-yl)oxy)dimethylsilane

: 945402-31-3
((2S,3S,4S)-1-(4-methoxybenzyloxy)-6-iodo-2,4-dimethylhex-5-yn-3-yloxy)(tert-butyl)dimethylsilane

Guidance literature:: (+)-tert-butyl(((2S,3S,4S)-1-((4-methoxybenzyl)oxy)-2,4-dimethylhex-5-yn-3-yl)oxy)dimethylsilane; With n-butyllithium; In tetrahydrofuran; hexane; at -50 ℃; for 1.11667h;

With iodine; In tetrahydrofuran; hexane; at -50 - 20 ℃; for 0.833333h; Further stages.;
DOI:10.1021/jm061385k

Reference yield:

: 945402-30-2
(2S,3S,4S)-1-((4-methoxybenzyl)oxy)-2,4-dimethylhex-5-en-3-ol

: 945402-31-3
((2S,3S,4S)-1-(4-methoxybenzyloxy)-6-iodo-2,4-dimethylhex-5-yn-3-yloxy)(tert-butyl)dimethylsilane

Guidance literature:: Multi-step reaction with 5 steps

1.1: 82 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / -78 - 20 °C

2.1: 2,6-lutidine; OsO₄; NaIO₄ / dioxane; H₂O; 2-methyl-propan-2-ol / 6 h / 20 °C

3.1: PPh₃ / CH₂Cl₂ / 0.28 h / 0 °C

3.2: 2,6-lutidine / CH₂Cl₂ / 0.17 h

3.3: 4.20 g / CH₂Cl₂ / 1 h

4.1: 96 percent / n-butyllithium / tetrahydrofuran; hexane / 3.17 h / -78 °C

5.1: n-butyllithium / tetrahydrofuran; hexane / 1.12 h / -50 °C

5.2: 99 percent / I₂ / tetrahydrofuran; hexane / 0.83 h / -50 - 20 °C

With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; n-butyllithium; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; water; tert-butyl alcohol; 3.2: Corey-Fuchs dibromoolefination;
DOI:10.1021/jm061385k

Reference yield:

: 945402-06-2
((2S,3S,4S)-1-(4-methoxybenzyloxy)-2,4-dimethylhex-5-en-3-yloxy)(tert-butyl)dimethylsilane

: 945402-31-3
((2S,3S,4S)-1-(4-methoxybenzyloxy)-6-iodo-2,4-dimethylhex-5-yn-3-yloxy)(tert-butyl)dimethylsilane

Guidance literature:: Multi-step reaction with 4 steps

1.1: 2,6-lutidine; OsO₄; NaIO₄ / dioxane; H₂O; 2-methyl-propan-2-ol / 6 h / 20 °C

2.1: PPh₃ / CH₂Cl₂ / 0.28 h / 0 °C

2.2: 2,6-lutidine / CH₂Cl₂ / 0.17 h

2.3: 4.20 g / CH₂Cl₂ / 1 h

3.1: 96 percent / n-butyllithium / tetrahydrofuran; hexane / 3.17 h / -78 °C

4.1: n-butyllithium / tetrahydrofuran; hexane / 1.12 h / -50 °C

4.2: 99 percent / I₂ / tetrahydrofuran; hexane / 0.83 h / -50 - 20 °C

With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; n-butyllithium; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; water; tert-butyl alcohol; 2.2: Corey-Fuchs dibromoolefination;
DOI:10.1021/jm061385k