2-(trimethylsilyl)ethyl 2-(benzyloxy)-6-(3-((2S,6S)-6-vinyltetrahydro-2H-pyran-2-yl)propyl)benzoate

Base Information

Chemical Name:2-(trimethylsilyl)ethyl 2-(benzyloxy)-6-(3-((2S,6S)-6-vinyltetrahydro-2H-pyran-2-yl)propyl)benzoate
CAS No.:1325653-39-1
Molecular Formula:C₂₉H₄₀O₄Si
Molecular Weight:480.72
Hs Code.:

Synonyms:2-(trimethylsilyl)ethyl 2-(benzyloxy)-6-(3-((2S,6S)-6-vinyltetrahydro-2H-pyran-2-yl)propyl)benzoate

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Chemical Property of 2-(trimethylsilyl)ethyl 2-(benzyloxy)-6-(3-((2S,6S)-6-vinyltetrahydro-2H-pyran-2-yl)propyl)benzoate

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Technology Process of 2-(trimethylsilyl)ethyl 2-(benzyloxy)-6-(3-((2S,6S)-6-vinyltetrahydro-2H-pyran-2-yl)propyl)benzoate

There total 16 articles about 2-(trimethylsilyl)ethyl 2-(benzyloxy)-6-(3-((2S,6S)-6-vinyltetrahydro-2H-pyran-2-yl)propyl)benzoate 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: 96.0%

: 1325653-78-8
2-(trimethylsilyl)ethyl 2-hydroxy-6-(3-((2S,6S)-6-vinyltetrahydro-2H-pyran-2-yl)propyl)benzoate

: 100-39-0
benzyl bromide

: 1325653-39-1
2-(trimethylsilyl)ethyl 2-(benzyloxy)-6-(3-((2S,6S)-6-vinyltetrahydro-2H-pyran-2-yl)propyl)benzoate

Guidance literature:: With caesium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 2h; Inert atmosphere;
DOI:10.1021/ol201863b

Reference yield:

: 886747-44-0
4-(2,2-dimethyl-4-oxo-4H-benzo[d][1,3]dioxin-5-yl)butanal

: 1325653-39-1
2-(trimethylsilyl)ethyl 2-(benzyloxy)-6-(3-((2S,6S)-6-vinyltetrahydro-2H-pyran-2-yl)propyl)benzoate

Guidance literature:: Multi-step reaction with 9 steps

1.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane; benzene / 2 h / -78 °C / Inert atmosphere

2.1: palladium 10% on activated carbon; hydrogen / methanol / 4 h

3.1: sodium iodide / acetone / 12 h / Reflux; Inert atmosphere

4.1: N,N-dimethyl-formamide / 12 h / 100 °C / Inert atmosphere

5.1: scandium tris(trifluoromethanesulfonate) / methanol / 24 h / 20 °C / Inert atmosphere

6.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / -78 °C / Inert atmosphere

7.1: sodium hexamethyldisilazane / tetrahydrofuran / -78 °C / Inert atmosphere

8.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

8.2: 3.5 h / 0 - 20 °C / Inert atmosphere

9.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

With oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; palladium 10% on activated carbon; hydrogen; sodium hexamethyldisilazane; caesium carbonate; dimethyl sulfoxide; triethylamine; sodium iodide; scandium tris(trifluoromethanesulfonate); In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; benzene; 6.1: Swern oxidation / 7.1: Julia-Kocienski olefination;
DOI:10.1021/ol201863b

Reference yield:

: 934560-37-9
5-(4-hydroxybutyl)-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one

: 1325653-39-1
2-(trimethylsilyl)ethyl 2-(benzyloxy)-6-(3-((2S,6S)-6-vinyltetrahydro-2H-pyran-2-yl)propyl)benzoate

Guidance literature:: Multi-step reaction with 10 steps

1.1: pyridinium chlorochromate / dichloromethane / 3 h / 20 °C / Molecular sieve; Inert atmosphere

2.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane; benzene / 2 h / -78 °C / Inert atmosphere

3.1: palladium 10% on activated carbon; hydrogen / methanol / 4 h

4.1: sodium iodide / acetone / 12 h / Reflux; Inert atmosphere

5.1: N,N-dimethyl-formamide / 12 h / 100 °C / Inert atmosphere

6.1: scandium tris(trifluoromethanesulfonate) / methanol / 24 h / 20 °C / Inert atmosphere

7.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / -78 °C / Inert atmosphere

8.1: sodium hexamethyldisilazane / tetrahydrofuran / -78 °C / Inert atmosphere

9.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

9.2: 3.5 h / 0 - 20 °C / Inert atmosphere

10.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

With oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; palladium 10% on activated carbon; hydrogen; sodium hexamethyldisilazane; caesium carbonate; dimethyl sulfoxide; triethylamine; pyridinium chlorochromate; sodium iodide; scandium tris(trifluoromethanesulfonate); In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; benzene; 7.1: Swern oxidation / 8.1: Julia-Kocienski olefination;
DOI:10.1021/ol201863b