(2S,3R,4R,5R)-3-acetoxy-4-dimethylphenylsilyl-2,4-dimethyl-5-ethyltetrahydrofuran-2-carboxylic acid ethyl ester

Base Information

Chemical Name:(2S,3R,4R,5R)-3-acetoxy-4-dimethylphenylsilyl-2,4-dimethyl-5-ethyltetrahydrofuran-2-carboxylic acid ethyl ester
CAS No.:548488-21-7
Molecular Formula:C₂₁H₃₂O₅Si
Molecular Weight:392.568
Hs Code.:

Synonyms:(2S,3R,4R,5R)-3-acetoxy-4-dimethylphenylsilyl-2,4-dimethyl-5-ethyltetrahydrofuran-2-carboxylic acid ethyl ester

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Chemical Property of (2S,3R,4R,5R)-3-acetoxy-4-dimethylphenylsilyl-2,4-dimethyl-5-ethyltetrahydrofuran-2-carboxylic acid ethyl ester

Chemical Property:

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Technology Process of (2S,3R,4R,5R)-3-acetoxy-4-dimethylphenylsilyl-2,4-dimethyl-5-ethyltetrahydrofuran-2-carboxylic acid ethyl ester

There total 1 articles about (2S,3R,4R,5R)-3-acetoxy-4-dimethylphenylsilyl-2,4-dimethyl-5-ethyltetrahydrofuran-2-carboxylic acid ethyl ester 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:

: 617-35-6
2-oxo-propionic acid ethyl ester

: 548488-19-3
(-)-acetic acid 2-methyl-3-(dimethylphenylsilyl)-(E)-pent-1-enyl ester

: 548488-21-7
(2S,3R,4R,5R)-3-acetoxy-4-dimethylphenylsilyl-2,4-dimethyl-5-ethyltetrahydrofuran-2-carboxylic acid ethyl ester

Guidance literature:: With tin(IV) chloride; triethylamine; In dichloromethane; at -78 ℃;
DOI:10.1021/ja034865z

Reference yield:

: 548488-21-7
(2S,3R,4R,5R)-3-acetoxy-4-dimethylphenylsilyl-2,4-dimethyl-5-ethyltetrahydrofuran-2-carboxylic acid ethyl ester

: 548488-22-8
(2R,3R,4R,5R)-4-dimethylphenylsilyl-3-hydroxy-2-hydroxymethyl-2,4-dimethyl-5-ethyltetrahydrofuran

Guidance literature:: With lithium aluminium tetrahydride; In diethyl ether; at 23 ℃;
DOI:10.1021/ja034865z

Reference yield:

: 548488-21-7
(2S,3R,4R,5R)-3-acetoxy-4-dimethylphenylsilyl-2,4-dimethyl-5-ethyltetrahydrofuran-2-carboxylic acid ethyl ester

: 548488-07-9
2,2-dimethyl propionic acid (R)-[(1R,2R)-1-benzyloxy-1-methyl-2-hydroxybutyl]-2-methylallyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: LiAlH₄ / diethyl ether / 23 °C

2.1: NaH / dimethylformamide / 0.5 h / 23 °C

2.2: 96 percent / n-Bu₄NI / dimethylformamide / 12 h / 23 °C

3.1: 85 percent / KH; cumene hydroperoxide; NMP / n-Bu₄NF / tetrahydrofuran / 15 h / 60 °C

4.1: NaH / dimethylformamide / 0.5 h / 0 °C

4.2: 95 percent / n-Bu₄NI / dimethylformamide / 12 h / 23 °C

5.1: 96 percent / NaHCO₃; aq. ceric ammonium nitrate; NaHSO₃ / acetonitrile / 1 h / 23 °C

6.1: 78 percent / Ph₃P; imidazole; I₂ / benzene / 1 h / Heating

7.1: 100 percent / Sc(OTf)3 / acetonitrile / 1 h / 23 °C

8.1: 83 percent / Zn; AcOH / methanol; diethyl ether / 12 h / 23 °C

With 1H-imidazole; 1-methyl-pyrrolidin-2-one; lithium aluminium tetrahydride; ammonium cerium(IV) nitrate; Cumene hydroperoxide; iodine; potassium hydride; sodium hydride; sodium hydrogencarbonate; sodium hydrogensulfite; acetic acid; triphenylphosphine; scandium tris(trifluoromethanesulfonate); zinc; tetrabutyl ammonium fluoride; In tetrahydrofuran; methanol; diethyl ether; N,N-dimethyl-formamide; acetonitrile; benzene;
DOI:10.1021/ja034865z