(2R,3R,4R,5R)-4-benzyloxy-2,4-dimethyl-5-ethyl-3-hydroxy-2-hydroxymethyltetrahydrofuran

Base Information

Chemical Name:(2R,3R,4R,5R)-4-benzyloxy-2,4-dimethyl-5-ethyl-3-hydroxy-2-hydroxymethyltetrahydrofuran
CAS No.:98004-04-7
Molecular Formula:C₁₆H₂₄O₄
Molecular Weight:280.364
Hs Code.:

Synonyms:(2R,3R,4R,5R)-4-benzyloxy-2,4-dimethyl-5-ethyl-3-hydroxy-2-hydroxymethyltetrahydrofuran

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Chemical Property of (2R,3R,4R,5R)-4-benzyloxy-2,4-dimethyl-5-ethyl-3-hydroxy-2-hydroxymethyltetrahydrofuran

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Technology Process of (2R,3R,4R,5R)-4-benzyloxy-2,4-dimethyl-5-ethyl-3-hydroxy-2-hydroxymethyltetrahydrofuran

There total 14 articles about (2R,3R,4R,5R)-4-benzyloxy-2,4-dimethyl-5-ethyl-3-hydroxy-2-hydroxymethyltetrahydrofuran 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%

: 548488-05-7
(2R,3R,4R,5R)-4-benzyloxy-2,4-dimethyl-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:: With ammonium cerium(IV) nitrate; sodium hydrogencarbonate; sodium hydrogensulfite; In acetonitrile; at 23 ℃; for 1h;
DOI:10.1021/ja034865z

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 4 steps

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

1.2: 96 percent / n-Bu₄NI / dimethylformamide / 12 h / 23 °C

2.1: 85 percent / KH; cumene hydroperoxide; NMP / n-Bu₄NF / tetrahydrofuran / 15 h / 60 °C

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

3.2: 95 percent / n-Bu₄NI / dimethylformamide / 12 h / 23 °C

4.1: 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

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 5 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

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