4-[(2S,3R,5R)-3-(benzyloxy)-5-methyl-5-propyltetrahydrofuran-2-yl]butan-2-one

Base Information

Chemical Name:4-[(2S,3R,5R)-3-(benzyloxy)-5-methyl-5-propyltetrahydrofuran-2-yl]butan-2-one
CAS No.:1374552-65-4
Molecular Formula:C₁₉H₂₈O₃
Molecular Weight:304.43
Hs Code.:

Synonyms:4-[(2S,3R,5R)-3-(benzyloxy)-5-methyl-5-propyltetrahydrofuran-2-yl]butan-2-one

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Chemical Property of 4-[(2S,3R,5R)-3-(benzyloxy)-5-methyl-5-propyltetrahydrofuran-2-yl]butan-2-one

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Technology Process of 4-[(2S,3R,5R)-3-(benzyloxy)-5-methyl-5-propyltetrahydrofuran-2-yl]butan-2-one

There total 16 articles about 4-[(2S,3R,5R)-3-(benzyloxy)-5-methyl-5-propyltetrahydrofuran-2-yl]butan-2-one 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: 92.0%

: C₂₀H₂₈O₃

: 1374552-65-4
4-[(2S,3R,5R)-3-(benzyloxy)-5-methyl-5-propyltetrahydrofuran-2-yl]butan-2-one

Guidance literature:: With palladium 10% on activated carbon; In methanol; at 20 ℃; for 0.5h;
DOI:10.1002/ejoc.201101605

Reference yield:

: 38084-00-3,131182-31-5
1-deoxy-1-iodo-2,3:4,6-di-O-isopropylidene-α-L-sorbofuranose

: 1374552-65-4
4-[(2S,3R,5R)-3-(benzyloxy)-5-methyl-5-propyltetrahydrofuran-2-yl]butan-2-one

Guidance literature:: Multi-step reaction with 15 steps

1.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / 10 h / 27 °C

2.1: sulfuric acid / methanol / 10 h / 27 °C

3.1: sodium hydride / N,N-dimethyl-formamide / 4 h / 0 - 27 °C

4.1: trifluoroborane diethyl ether / dichloromethane / 1 h / -78 - 27 °C

5.1: carbon disulfide; sodium hydride; methyl iodide / tetrahydrofuran / 3 h / 0 - 25 °C

5.2: 10 h / Reflux

6.1: ammonia; lithium / tetrahydrofuran / 1 h / -78 °C

7.1: triethylamine / dichloromethane / 1 h / 0 °C

8.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 7 h / 25 °C

9.1: lithium hydroxide / methanol; water / 0.5 h / 20 °C

10.1: sodium hydride / N,N-dimethyl-formamide / 3 h / 0 °C

11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 0 °C

12.1: hydrogen / ethanol / 1 h / 20 °C

13.1: Dess-Martin periodane / dichloromethane / 2 h / 25 °C

14.1: benzene / 2 h / Reflux

15.1: palladium 10% on activated carbon / methanol / 0.5 h / 20 °C

With carbon disulfide; 2,2'-azobis(isobutyronitrile); sulfuric acid; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; ammonia; hydrogen; tri-n-butyl-tin hydride; trifluoroborane diethyl ether; lithium; sodium hydride; Dess-Martin periodane; triethylamine; triphenylphosphine; lithium hydroxide; diethylazodicarboxylate; methyl iodide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; benzene; 5.1: Barton-McCombie deoxygenation / 5.2: Barton-McCombie deoxygenation / 8.1: Mitsunobu reaction / 13.1: Dess-Martin oxidation;
DOI:10.1002/ejoc.201101605

Reference yield:

: 1374552-72-3
C₁₆H₂₂O₃

: 1374552-65-4
4-[(2S,3R,5R)-3-(benzyloxy)-5-methyl-5-propyltetrahydrofuran-2-yl]butan-2-one

Guidance literature:: Multi-step reaction with 4 steps

1: hydrogen / ethanol / 1 h / 20 °C

2: Dess-Martin periodane / dichloromethane / 2 h / 25 °C

3: benzene / 2 h / Reflux

4: palladium 10% on activated carbon / methanol / 0.5 h / 20 °C

With palladium 10% on activated carbon; hydrogen; Dess-Martin periodane; In methanol; ethanol; dichloromethane; benzene; 2: Dess-Martin oxidation;
DOI:10.1002/ejoc.201101605