tert-butyl((2R,4R,6S)-2-((E)-3-iodo-2-methylallyl)-6-((E)-3-methyl-5-phenylpent-3-enyl)tetrahydro-2H-pyran-4-yloxy)dimethylsilane

Base Information

• Chemical Name: tert-butyl((2R,4R,6S)-2-((E)-3-iodo-2-methylallyl)-6-((E)-3-methyl-5-phenylpent-3-enyl)tetrahydro-2H-pyran-4-yloxy)dimethylsilane
• CAS No.: 1375950-99-4
• Molecular Formula: C₂₇H₄₃IO₂Si
• Molecular Weight: 554.627

Synonyms:tert-butyl((2R,4R,6S)-2-((E)-3-iodo-2-methylallyl)-6-((E)-3-methyl-5-phenylpent-3-enyl)tetrahydro-2H-pyran-4-yloxy)dimethylsilane

Chemical Property of tert-butyl((2R,4R,6S)-2-((E)-3-iodo-2-methylallyl)-6-((E)-3-methyl-5-phenylpent-3-enyl)tetrahydro-2H-pyran-4-yloxy)dimethylsilane

Chemical Property:

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Technology Process of tert-butyl((2R,4R,6S)-2-((E)-3-iodo-2-methylallyl)-6-((E)-3-methyl-5-phenylpent-3-enyl)tetrahydro-2H-pyran-4-yloxy)dimethylsilane

There total 9 articles about tert-butyl((2R,4R,6S)-2-((E)-3-iodo-2-methylallyl)-6-((E)-3-methyl-5-phenylpent-3-enyl)tetrahydro-2H-pyran-4-yloxy)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: 48.0%

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 (1375950-86-9) + trimethylaluminum (75-24-1) → tert-butyl((2R,4R,6S)-2-((E)-3-iodo-2-methylallyl)-6-((E)-3-methyl-5-phenylpent-3-enyl)tetrahydro-2H-pyran-4-yloxy)dimethylsilane (1375950-99-4)

Guidance literature:

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; trimethylaluminum; With zirconocene dichloride; tert-butyl alcohol; In dichloromethane; toluene; at 0 - 20 ℃; Inert atmosphere;

With iodine; In tetrahydrofuran; dichloromethane; toluene; at -20 - 20 ℃; Inert atmosphere;

DOI:10.1002/anie.201108749

Reference yield:

(2S,4R,6R)-2-(but-3-ynyl)-6-(3-(trimethylsilyl)prop-2-ynyl)tetrahydro-2H-pyran-4-ol (1375950-97-2) → tert-butyl((2R,4R,6S)-2-((E)-3-iodo-2-methylallyl)-6-((E)-3-methyl-5-phenylpent-3-enyl)tetrahydro-2H-pyran-4-yloxy)dimethylsilane (1375950-99-4)

Guidance literature:

Multi-step reaction with 5 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

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

5.2: -20 - 20 °C / Inert atmosphere

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

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → tert-butyl((2R,4R,6S)-2-((E)-3-iodo-2-methylallyl)-6-((E)-3-methyl-5-phenylpent-3-enyl)tetrahydro-2H-pyran-4-yloxy)dimethylsilane (1375950-99-4)

Guidance literature:

Multi-step reaction with 5 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

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

5.2: -20 - 20 °C / Inert atmosphere

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

upstream raw materials:

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

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

(2S,4R,6R)-2-(but-3-ynyl)-tetrahydro-6-(3-(trimethylsilyl)prop-2-ynyl)-2H-pyran-4-yl-2,2,2-trifluoroacetate

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

Downstream raw materials:

(2R,4R,6S)-2-((E)-3-iodo-2-methylallyl)-6-((E)-3-methyl-5-phenylpent-3-enyl)tetrahydro-2H-pyran-4-ol

(2S,4S,6R)-2-((E)-3-methyl-5-phenylpent-3-en-1-yl)-6-((E)-2-methylhexa-2,5-dien-1-yl)tetrahydro-2H-pyran-4-yl-(E)-3-(2-((tert-butyldimethylsilyl)oxy)ethyl)hexa-2,5-dienoate

(1S,4E,7E,10E,13R,15S)-5-(2-hydroxyethyl)-11-methyl-15-((E)-3-methyl-5-phenylpent-3-enyl)-2,14-dioxabicyclo[11.3.1]heptadeca-4,7,10-trien-3-one

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