(2R,3R,4R,5R)-2,4-dimethyl-4-dimethylphenylsilyl-5-ethyl-3-(p-methoxybenzyloxy)-2-(p-methoxybenzyloxymethyl)tetrahydrofuran

Base Information

Chemical Name:(2R,3R,4R,5R)-2,4-dimethyl-4-dimethylphenylsilyl-5-ethyl-3-(p-methoxybenzyloxy)-2-(p-methoxybenzyloxymethyl)tetrahydrofuran
CAS No.:548488-03-5
Molecular Formula:C₃₃H₄₄O₅Si
Molecular Weight:548.795
Hs Code.:

Synonyms:(2R,3R,4R,5R)-2,4-dimethyl-4-dimethylphenylsilyl-5-ethyl-3-(p-methoxybenzyloxy)-2-(p-methoxybenzyloxymethyl)tetrahydrofuran

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Chemical Property of (2R,3R,4R,5R)-2,4-dimethyl-4-dimethylphenylsilyl-5-ethyl-3-(p-methoxybenzyloxy)-2-(p-methoxybenzyloxymethyl)tetrahydrofuran

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Technology Process of (2R,3R,4R,5R)-2,4-dimethyl-4-dimethylphenylsilyl-5-ethyl-3-(p-methoxybenzyloxy)-2-(p-methoxybenzyloxymethyl)tetrahydrofuran

There total 1 articles about (2R,3R,4R,5R)-2,4-dimethyl-4-dimethylphenylsilyl-5-ethyl-3-(p-methoxybenzyloxy)-2-(p-methoxybenzyloxymethyl)tetrahydrofuran 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:

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

: 548488-03-5
(2R,3R,4R,5R)-2,4-dimethyl-4-dimethylphenylsilyl-5-ethyl-3-(p-methoxybenzyloxy)-2-(p-methoxybenzyloxymethyl)tetrahydrofuran

Guidance literature:: Multi-step reaction with 2 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

With lithium aluminium tetrahydride; sodium hydride; In diethyl ether; N,N-dimethyl-formamide;
DOI:10.1021/ja034865z

Reference yield: 85.0%

: 548488-03-5
(2R,3R,4R,5R)-2,4-dimethyl-4-dimethylphenylsilyl-5-ethyl-3-(p-methoxybenzyloxy)-2-(p-methoxybenzyloxymethyl)tetrahydrofuran

: 548488-04-6
(2R,3R,4R,5R)-2,4-dimethyl-5-ethyl-4-hydroxy-3-(p-methoxybenzyloxy)-2-(p-methoxybenzyloxymethyl)tetrahydrofuran

Guidance literature:: With 1-methyl-pyrrolidin-2-one; Cumene hydroperoxide; potassium hydride; tetrabutyl ammonium fluoride; In tetrahydrofuran; at 60 ℃; for 15h;
DOI:10.1021/ja034865z

Reference yield:

: 548488-03-5
(2R,3R,4R,5R)-2,4-dimethyl-4-dimethylphenylsilyl-5-ethyl-3-(p-methoxybenzyloxy)-2-(p-methoxybenzyloxymethyl)tetrahydrofuran

: 98004-04-7
(2R,3R,4R,5R)-4-benzyloxy-2,4-dimethyl-5-ethyl-3-hydroxy-2-hydroxymethyltetrahydrofuran

Guidance literature:: Multi-step reaction with 3 steps

1.1: 85 percent / KH; cumene hydroperoxide; NMP / n-Bu₄NF / tetrahydrofuran / 15 h / 60 °C

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

2.2: 95 percent / n-Bu₄NI / dimethylformamide / 12 h / 23 °C

3.1: 96 percent / NaHCO₃; aq. ceric ammonium nitrate; NaHSO₃ / acetonitrile / 1 h / 23 °C

With 1-methyl-pyrrolidin-2-one; ammonium cerium(IV) nitrate; Cumene hydroperoxide; potassium hydride; sodium hydride; sodium hydrogencarbonate; sodium hydrogensulfite; tetrabutyl ammonium fluoride; In tetrahydrofuran; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ja034865z