(2R,3R,5R)-5-(2,6-dichlorobenzyloxymethyl)-3-methyltetrahydrofuran-2-carbaldehyde

Base Information

Chemical Name:(2R,3R,5R)-5-(2,6-dichlorobenzyloxymethyl)-3-methyltetrahydrofuran-2-carbaldehyde
CAS No.:625822-06-2
Molecular Formula:C₁₄H₁₆Cl₂O₃
Molecular Weight:303.185
Hs Code.:

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

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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,5R)-5-(2,6-dichlorobenzyloxymethyl)-3-methyltetrahydrofuran-2-carbaldehyde

Chemical Property:

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

There total 12 articles about (2R,3R,5R)-5-(2,6-dichlorobenzyloxymethyl)-3-methyltetrahydrofuran-2-carbaldehyde 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: 93.0%

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

: 625822-06-2
(2R,3R,5R)-5-(2,6-dichlorobenzyloxymethyl)-3-methyltetrahydrofuran-2-carbaldehyde

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 20 ℃;
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

: 625822-06-2
(2R,3R,5R)-5-(2,6-dichlorobenzyloxymethyl)-3-methyltetrahydrofuran-2-carbaldehyde

Guidance literature:: Multi-step reaction with 11 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

11.1: 93 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

With 1H-imidazole; oxalyl dichloride; 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; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 11.1: Swern oxidation;
DOI:10.1021/jo062396o

Reference yield:

: 625822-04-0
(2R,3R,4S,5R)-5-(tert-butyldimethylsilanyloxymethyl)-2-(2,6-dichlorobenzyloxymethyl)-4-methyltetrahydrofuran-2-ol

: 625822-06-2
(2R,3R,5R)-5-(2,6-dichlorobenzyloxymethyl)-3-methyltetrahydrofuran-2-carbaldehyde

Guidance literature:: Multi-step reaction with 4 steps

1: 92 percent / toluene / 3 h / 100 °C

2: 96 percent / n-Bu₃SnH; AIBN / toluene / 0.58 h / 100 °C

3: 95 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

4: 93 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

With oxalyl dichloride; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; toluene; 4: Swern oxidation;
DOI:10.1021/jo062396o