(4R,5S,6S)-4-(2-(benzyloxy)ethyl)-6-ethyl-5-methyl-4-(trimethylsilyloxy)-tetrahydropyran-2-one

Base Information

Chemical Name:(4R,5S,6S)-4-(2-(benzyloxy)ethyl)-6-ethyl-5-methyl-4-(trimethylsilyloxy)-tetrahydropyran-2-one
CAS No.:1299358-23-8
Molecular Formula:C₂₀H₃₂O₄Si
Molecular Weight:364.557
Hs Code.:

Synonyms:(4R,5S,6S)-4-(2-(benzyloxy)ethyl)-6-ethyl-5-methyl-4-(trimethylsilyloxy)-tetrahydropyran-2-one

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Chemical Property of (4R,5S,6S)-4-(2-(benzyloxy)ethyl)-6-ethyl-5-methyl-4-(trimethylsilyloxy)-tetrahydropyran-2-one

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Technology Process of (4R,5S,6S)-4-(2-(benzyloxy)ethyl)-6-ethyl-5-methyl-4-(trimethylsilyloxy)-tetrahydropyran-2-one

There total 10 articles about (4R,5S,6S)-4-(2-(benzyloxy)ethyl)-6-ethyl-5-methyl-4-(trimethylsilyloxy)-tetrahydropyran-2-one 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%

: 75-77-4
chloro-trimethyl-silane

: 1299358-22-7
(4R,5S,6S)-4-(2-(benzyloxy)ethyl)-6-ethyl-4-hydroxy-5-methyl-tetrahydropyran-2-one

: 1299358-23-8
(4R,5S,6S)-4-(2-(benzyloxy)ethyl)-6-ethyl-5-methyl-4-(trimethylsilyloxy)-tetrahydropyran-2-one

Guidance literature:: With 1H-imidazole; dmap; In dichloromethane; at 20 ℃; for 4h; Inert atmosphere;
DOI:10.1055/s-0030-1259286

Reference yield:

: 1299358-21-6
(1S,2S)-5-(benzyloxy)-1-ethyl-2-methyl-3-oxopentyl bromoacetate

: 1299358-23-8
(4R,5S,6S)-4-(2-(benzyloxy)ethyl)-6-ethyl-5-methyl-4-(trimethylsilyloxy)-tetrahydropyran-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: samarium diiodide / tetrahydrofuran / -78 °C / Inert atmosphere

2: 1H-imidazole; dmap / dichloromethane / 4 h / 20 °C / Inert atmosphere

With 1H-imidazole; dmap; samarium diiodide; In tetrahydrofuran; dichloromethane; 1: intramolecular Reformatsky reaction;
DOI:10.1055/s-0030-1259286

Reference yield:

: methyl (3S)-3-hydroxy-2-methylpentanoate

: 1299358-23-8
(4R,5S,6S)-4-(2-(benzyloxy)ethyl)-6-ethyl-5-methyl-4-(trimethylsilyloxy)-tetrahydropyran-2-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: 1H-imidazole; dmap / N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere

2.1: isopropyl magnesium bromide/chloride / tetrahydrofuran / 0.25 h / -10 °C / Inert atmosphere

2.2: 2 h / -10 - 20 °C / Inert atmosphere

3.1: tetrahydrofuran / -10 - 0 °C / Inert atmosphere

4.1: N,N,N',N'-tetramethylguanidine / 2 h / 20 °C / Inert atmosphere

5.1: hydrogenchloride; water / methanol / 2 h / 20 °C

6.1: pyridine; dmap / dichloromethane / -78 - -10 °C / Inert atmosphere

7.1: samarium diiodide / tetrahydrofuran / -78 °C / Inert atmosphere

8.1: 1H-imidazole; dmap / dichloromethane / 4 h / 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; hydrogenchloride; dmap; samarium diiodide; water; N,N,N',N'-tetramethylguanidine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 3.1: Grignard reaction / 4.1: Michael addition / 7.1: intramolecular Reformatsky reaction;
DOI:10.1055/s-0030-1259286