(1R)-2-(benzyloxy)-1-[(2S,4R)-4-ethyl-5-oxotetrahydrofuran-2-yl]ethyl methanesulfonate

Base Information

Chemical Name:(1R)-2-(benzyloxy)-1-[(2S,4R)-4-ethyl-5-oxotetrahydrofuran-2-yl]ethyl methanesulfonate
CAS No.:1000052-62-9
Molecular Formula:C₁₆H₂₂O₆S
Molecular Weight:342.413
Hs Code.:

Synonyms:(1R)-2-(benzyloxy)-1-[(2S,4R)-4-ethyl-5-oxotetrahydrofuran-2-yl]ethyl methanesulfonate

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Chemical Property of (1R)-2-(benzyloxy)-1-[(2S,4R)-4-ethyl-5-oxotetrahydrofuran-2-yl]ethyl methanesulfonate

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Technology Process of (1R)-2-(benzyloxy)-1-[(2S,4R)-4-ethyl-5-oxotetrahydrofuran-2-yl]ethyl methanesulfonate

There total 4 articles about (1R)-2-(benzyloxy)-1-[(2S,4R)-4-ethyl-5-oxotetrahydrofuran-2-yl]ethyl methanesulfonate 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%

: 1000052-60-7
(3R,5S)-5-[(1R)-2-(benzyloxy)-1-hydroxyethyl]-3-ethyldihydrofuran-2(3H)-one

: 124-63-0
methanesulfonyl chloride

: 1000052-62-9
(1R)-2-(benzyloxy)-1-[(2S,4R)-4-ethyl-5-oxotetrahydrofuran-2-yl]ethyl methanesulfonate

Guidance literature:: With triethylamine; In dichloromethane; at 0 ℃; for 3h;

Reference yield:

: 89358-30-5
benzyl (2E)-4-bromobut-2-en-1-yl ether

: 1000052-62-9
(1R)-2-(benzyloxy)-1-[(2S,4R)-4-ethyl-5-oxotetrahydrofuran-2-yl]ethyl methanesulfonate

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium hexamethyldisilazane / hexane; tetrahydrofuran / 1.25 h / -78 °C / Inert atmosphere

1.2: 5 h / -78 - -40 °C / Inert atmosphere

2.1: dihydrogen peroxide; lithium hydroxide monohydrate / tetrahydrofuran; water / 13 h / 0 - 20 °C

3.1: tetra(n-butyl)ammonium hydrogensulfate; Shi's ketone; Oxone; potassium carbonate / acetonitrile / 5 h / 0 °C

4.1: triethylamine / dichloromethane / 3 h / 0 °C

With Oxone; Shi's ketone; lithium hydroxide monohydrate; dihydrogen peroxide; tetra(n-butyl)ammonium hydrogensulfate; sodium hexamethyldisilazane; potassium carbonate; triethylamine; In tetrahydrofuran; hexane; dichloromethane; water; acetonitrile; 3.1: |Shi Asymmetric Epoxidation;
DOI:10.1021/ml300168e

Reference yield:

: 1000052-53-8
(4S)-4-benzyl-3-[(2R,4E)-6-(benzyloxy)-2-ethylhex-4-enoyl]-1,3-oxazolidin-2-one

: 1000052-62-9
(1R)-2-(benzyloxy)-1-[(2S,4R)-4-ethyl-5-oxotetrahydrofuran-2-yl]ethyl methanesulfonate

Guidance literature:: Multi-step reaction with 3 steps

1: dihydrogen peroxide; lithium hydroxide monohydrate / tetrahydrofuran; water / 13 h / 0 - 20 °C

2: tetra(n-butyl)ammonium hydrogensulfate; Shi's ketone; Oxone; potassium carbonate / acetonitrile / 5 h / 0 °C

3: triethylamine / dichloromethane / 3 h / 0 °C

With Oxone; Shi's ketone; lithium hydroxide monohydrate; dihydrogen peroxide; tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate; triethylamine; In tetrahydrofuran; dichloromethane; water; acetonitrile; 2: |Shi Asymmetric Epoxidation;
DOI:10.1021/ml300168e