(2R,4S,5R)-4-methyl-5-(2-hydroxy-ethyl)tetrahydro-2-furanyl-(1R,2S)-2-phenylcyclohexyl ether

Base Information

Chemical Name:(2R,4S,5R)-4-methyl-5-(2-hydroxy-ethyl)tetrahydro-2-furanyl-(1R,2S)-2-phenylcyclohexyl ether
CAS No.:268736-31-8
Molecular Formula:C₁₉H₂₈O₃
Molecular Weight:304.43
Hs Code.:

Synonyms:(2R,4S,5R)-4-methyl-5-(2-hydroxy-ethyl)tetrahydro-2-furanyl-(1R,2S)-2-phenylcyclohexyl ether

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Chemical Property of (2R,4S,5R)-4-methyl-5-(2-hydroxy-ethyl)tetrahydro-2-furanyl-(1R,2S)-2-phenylcyclohexyl ether

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Technology Process of (2R,4S,5R)-4-methyl-5-(2-hydroxy-ethyl)tetrahydro-2-furanyl-(1R,2S)-2-phenylcyclohexyl ether

There total 4 articles about (2R,4S,5R)-4-methyl-5-(2-hydroxy-ethyl)tetrahydro-2-furanyl-(1R,2S)-2-phenylcyclohexyl ether 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%

: 268736-27-2
(2S,4S,5R)-4-methyl-5-vinyltetrahydro-2-fyranyl (1R,2S)-2-phenylcyclohexyl ether

: 268736-31-8
(2R,4S,5R)-4-methyl-5-(2-hydroxy-ethyl)tetrahydro-2-furanyl-(1R,2S)-2-phenylcyclohexyl ether

Guidance literature:: (2S,4S,5R)-4-methyl-5-vinyltetrahydro-2-fyranyl (1R,2S)-2-phenylcyclohexyl ether; With 9-borabicyclo[3.3.1]nonane dimer; In tetrahydrofuran; for 3h; Heating;

With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran; at 20 ℃; for 1h; Further stages.;
DOI:10.1021/ol005613v

Reference yield:

: 2-bromo-1-[(1R,2S)-(2-phenylcyclohexyl)oxy]ethyl 1-vinyl-2-propenyl ether

: 268736-31-8
(2R,4S,5R)-4-methyl-5-(2-hydroxy-ethyl)tetrahydro-2-furanyl-(1R,2S)-2-phenylcyclohexyl ether

Guidance literature:: Multi-step reaction with 2 steps

1.1: Bu₃SnH; Et₃B; O₂ / toluene; hexane / 3 h / -78 °C

2.1: 9-BBN / tetrahydrofuran / 3 h / Heating

2.2: 93 percent / aq. NaOH; H₂O₂ / tetrahydrofuran / 1 h / 20 °C

With 9-borabicyclo[3.3.1]nonane dimer; triethyl borane; oxygen; tri-n-butyl-tin hydride; In tetrahydrofuran; hexane; toluene;
DOI:10.1002/chem.200390180

Reference yield:

: 98919-68-7
(1R,2S)-trans-2-phenylcyclohexanol

: 268736-31-8
(2R,4S,5R)-4-methyl-5-(2-hydroxy-ethyl)tetrahydro-2-furanyl-(1R,2S)-2-phenylcyclohexyl ether

Guidance literature:: Multi-step reaction with 4 steps

1.1: 88 percent / Hg(OAc)2 / 48 h / Heating

2.1: 75 percent / NBS / CH₂Cl₂ / 3 h / -20 °C

3.1: 85 percent / Bu₃SnH; Et₃B; O₂ / toluene; hexane / 2 h / -78 °C

4.1: 9-BBN / tetrahydrofuran / 3 h / Heating

4.2: 93 percent / aq. H₂O₂; NaOH / tetrahydrofuran / 1 h / 20 °C

With N-Bromosuccinimide; 9-borabicyclo[3.3.1]nonane dimer; triethyl borane; mercury(II) diacetate; oxygen; tri-n-butyl-tin hydride; In tetrahydrofuran; hexane; dichloromethane; toluene; 1.1: transetherification / 2.1: Addition / 3.1: Ueno-Stork radical cyclization / 4.1: hydroboration / 4.2: Hydrolysis;
DOI:10.1021/ol005613v