tert-butyldimethyl (((2S,4R,6R)-2-((E)-3-methyl-5-phenylpent-3-en-1-yl)-6-(prop-2-yn-1-yl)tetrahydro-2H-pyran-4-yl)oxy)silane

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Chemical Name:tert-butyldimethyl (((2S,4R,6R)-2-((E)-3-methyl-5-phenylpent-3-en-1-yl)-6-(prop-2-yn-1-yl)tetrahydro-2H-pyran-4-yl)oxy)silane
CAS No.:1375950-86-9
Molecular Formula:C₂₆H₄₀O₂Si
Molecular Weight:412.688
Hs Code.:

Synonyms:tert-butyldimethyl (((2S,4R,6R)-2-((E)-3-methyl-5-phenylpent-3-en-1-yl)-6-(prop-2-yn-1-yl)tetrahydro-2H-pyran-4-yl)oxy)silane

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Chemical Property of tert-butyldimethyl (((2S,4R,6R)-2-((E)-3-methyl-5-phenylpent-3-en-1-yl)-6-(prop-2-yn-1-yl)tetrahydro-2H-pyran-4-yl)oxy)silane

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Technology Process of tert-butyldimethyl (((2S,4R,6R)-2-((E)-3-methyl-5-phenylpent-3-en-1-yl)-6-(prop-2-yn-1-yl)tetrahydro-2H-pyran-4-yl)oxy)silane

There total 10 articles about tert-butyldimethyl (((2S,4R,6R)-2-((E)-3-methyl-5-phenylpent-3-en-1-yl)-6-(prop-2-yn-1-yl)tetrahydro-2H-pyran-4-yl)oxy)silane 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: 88.0%

: 1375950-98-3
tert-butyldimethyl((2S,4R,6R)-2-((E)-3-methyl-5-phenylpent-3-enyl)-6-(3-(trimethylsilyl)prop-2-ynyl)tetrahydro-2H-pyran-4-yloxy)silane

: 1375950-86-9
tert-butyldimethyl (((2S,4R,6R)-2-((E)-3-methyl-5-phenylpent-3-en-1-yl)-6-(prop-2-yn-1-yl)tetrahydro-2H-pyran-4-yl)oxy)silane

Guidance literature:: With potassium carbonate; In tetrahydrofuran; methanol; at 0 - 20 ℃; for 3h;
DOI:10.1002/anie.201108749

Reference yield:

: 1375950-84-7
(3-((2R,4R,6S)-6-(but-3-ynyl)-4-(tert-butyldimethylsilyloxy)tetrahydro-2H-pyran-2-yl)prop-1-ynyl)trimethylsilane

: 1375950-86-9
tert-butyldimethyl (((2S,4R,6R)-2-((E)-3-methyl-5-phenylpent-3-en-1-yl)-6-(prop-2-yn-1-yl)tetrahydro-2H-pyran-4-yl)oxy)silane

Guidance literature:: Multi-step reaction with 3 steps

1.1: zirconocene dichloride; tert-butyl alcohol / dichloromethane; toluene / 24 h / 0 - 20 °C / Inert atmosphere

1.2: 5 h / 0 °C / Inert atmosphere

2.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran; 1-methyl-pyrrolidin-2-one / 60 h / 20 °C / Inert atmosphere

3.1: potassium carbonate / tetrahydrofuran; methanol / 3 h / 0 - 20 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; zirconocene dichloride; potassium carbonate; tert-butyl alcohol; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; dichloromethane; toluene; 2.1: Negishi coupling reaction;
DOI:10.1002/anie.201108749

Reference yield:

: 1375950-97-2
(2S,4R,6R)-2-(but-3-ynyl)-6-(3-(trimethylsilyl)prop-2-ynyl)tetrahydro-2H-pyran-4-ol

: 1375950-86-9
tert-butyldimethyl (((2S,4R,6R)-2-((E)-3-methyl-5-phenylpent-3-en-1-yl)-6-(prop-2-yn-1-yl)tetrahydro-2H-pyran-4-yl)oxy)silane

Guidance literature:: Multi-step reaction with 4 steps

1.1: 2,6-dimethylpyridine / dichloromethane / 2 h / -78 °C

2.1: zirconocene dichloride; tert-butyl alcohol / dichloromethane; toluene / 24 h / 0 - 20 °C / Inert atmosphere

2.2: 5 h / 0 °C / Inert atmosphere

3.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran; 1-methyl-pyrrolidin-2-one / 60 h / 20 °C / Inert atmosphere

4.1: potassium carbonate / tetrahydrofuran; methanol / 3 h / 0 - 20 °C

With 2,6-dimethylpyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; zirconocene dichloride; potassium carbonate; tert-butyl alcohol; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; dichloromethane; toluene; 3.1: Negishi coupling reaction;
DOI:10.1002/anie.201108749