(2R,3R,5S)-5-(2,6-dichlorobenzyloxymethyl)-3-methyltetrahydrofuran-2-ylmethanol

Base Information

Chemical Name:(2R,3R,5S)-5-(2,6-dichlorobenzyloxymethyl)-3-methyltetrahydrofuran-2-ylmethanol
CAS No.:625822-11-9
Molecular Formula:C₁₄H₁₈Cl₂O₃
Molecular Weight:305.201
Hs Code.:

Synonyms:(2R,3R,5S)-5-(2,6-dichlorobenzyloxymethyl)-3-methyltetrahydrofuran-2-ylmethanol

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2R,3R,5S)-5-(2,6-dichlorobenzyloxymethyl)-3-methyltetrahydrofuran-2-ylmethanol

Chemical Property:

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Technology Process of (2R,3R,5S)-5-(2,6-dichlorobenzyloxymethyl)-3-methyltetrahydrofuran-2-ylmethanol

There total 11 articles about (2R,3R,5S)-5-(2,6-dichlorobenzyloxymethyl)-3-methyltetrahydrofuran-2-ylmethanol 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: 95.0%

: 625822-05-1
(2R,3R,4S,5R)-tert-butyl-[5-(2,6-dichlorobenzyloxymethyl)-3-methyltetrahydrofuran-2-ylmethoxy]dimethylsilane

: 625822-11-9
(2R,3R,5S)-5-(2,6-dichlorobenzyloxymethyl)-3-methyltetrahydrofuran-2-ylmethanol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 2h;
DOI:10.1021/ol030101c DOI:10.1021/jo062396o

Reference yield:

: 88424-95-7
2,3-O-isopropylidene-1-C-<(1S)-1-methylprop-2-enyl>-D-erythro-glycerol

: 625822-11-9
(2R,3R,5S)-5-(2,6-dichlorobenzyloxymethyl)-3-methyltetrahydrofuran-2-ylmethanol

Guidance literature:: Multi-step reaction with 10 steps

1.1: 88 percent / NaH / dimethylformamide

2.1: 85 percent / p-TsOH / methanol

3.1: 92 percent / NaH; n-Bu₄NI / dimethylformamide / 20 °C

4.1: 87 percent / iodine / acetonitrile / 3 h / -20 °C

5.1: cesium trifluoroacetate / dimethylformamide / 36 h / 90 °C

5.2: 92 percent / diethylamine / dimethylformamide / 3 h / 20 °C

6.1: 95 percent / imidazole / dimethylformamide / 20 °C

7.1: 94 percent / DDQ / CH₂Cl₂ / 3 h / 20 °C / pH 7

8.1: 92 percent / toluene / 3 h / 100 °C

9.1: 96 percent / n-Bu₃SnH; AIBN / toluene / 0.58 h / 100 °C

10.1: 95 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

With 1H-imidazole; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; iodine; tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; sodium hydride; cesium trifluoroacetate; toluene-4-sulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1021/jo062396o

Reference yield:

: 625822-02-8
(2R,3R,4S,5R)-[5-(2,6-dichlorobenzyloxymethyl)-4-(4-methoxybenzyloxy)-3-methyltetrahydrofuran-2-yl]methanol

: 625822-11-9
(2R,3R,5S)-5-(2,6-dichlorobenzyloxymethyl)-3-methyltetrahydrofuran-2-ylmethanol

Guidance literature:: Multi-step reaction with 5 steps

1: 95 percent / imidazole / dimethylformamide / 20 °C

2: 94 percent / DDQ / CH₂Cl₂ / 3 h / 20 °C / pH 7

3: 92 percent / toluene / 3 h / 100 °C

4: 96 percent / n-Bu₃SnH; AIBN / toluene / 0.58 h / 100 °C

5: 95 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

With 1H-imidazole; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo062396o