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

Base Information

Chemical Name:(4R,5S,6S)-4-(2-(benzyloxy)ethyl)-6-ethyl-4-hydroxy-5-methyl-tetrahydropyran-2-one
CAS No.:1299358-22-7
Molecular Formula:C₁₇H₂₄O₄
Molecular Weight:292.375
Hs Code.:

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

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

Chemical Property:

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

There total 9 articles about (4R,5S,6S)-4-(2-(benzyloxy)ethyl)-6-ethyl-4-hydroxy-5-methyl-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: 88.0%

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

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

Guidance literature:: With samarium diiodide; In tetrahydrofuran; at -78 ℃; Inert atmosphere;
DOI:10.1055/s-0030-1259286

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 7 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

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

Reference yield:

: 1299358-18-1
(4S,5S)-1-(benzyloxy)-5-{[tert-butyl(dimethyl)silyl]oxy}-4-methylheptan-3-one

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

Guidance literature:: Multi-step reaction with 3 steps

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

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

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

With pyridine; hydrogenchloride; dmap; samarium diiodide; water; In tetrahydrofuran; methanol; dichloromethane; 3: intramolecular Reformatsky reaction;
DOI:10.1055/s-0030-1259286