2-((2R,3S,5R)-3-methyl-5-{[(1R,2S)-2-phenylcyclohexyl]oxy}tetrahydro-2-furanyl)acetaldehyde

Base Information

Chemical Name:2-((2R,3S,5R)-3-methyl-5-{[(1R,2S)-2-phenylcyclohexyl]oxy}tetrahydro-2-furanyl)acetaldehyde
CAS No.:268736-32-9
Molecular Formula:C₁₉H₂₆O₃
Molecular Weight:302.414
Hs Code.:

Synonyms:2-((2R,3S,5R)-3-methyl-5-{[(1R,2S)-2-phenylcyclohexyl]oxy}tetrahydro-2-furanyl)acetaldehyde

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Chemical Property of 2-((2R,3S,5R)-3-methyl-5-{[(1R,2S)-2-phenylcyclohexyl]oxy}tetrahydro-2-furanyl)acetaldehyde

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Technology Process of 2-((2R,3S,5R)-3-methyl-5-{[(1R,2S)-2-phenylcyclohexyl]oxy}tetrahydro-2-furanyl)acetaldehyde

There total 5 articles about 2-((2R,3S,5R)-3-methyl-5-{[(1R,2S)-2-phenylcyclohexyl]oxy}tetrahydro-2-furanyl)acetaldehyde 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%

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

: 268736-32-9
2-((2R,3S,5R)-3-methyl-5-{[(1R,2S)-2-phenylcyclohexyl]oxy}tetrahydro-2-furanyl)acetaldehyde

Guidance literature:: With oxalyl dichloride; In dichloromethane; dimethyl sulfoxide; at -78 ℃; for 0.5h;
DOI:10.1021/ol005613v

Reference yield:

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

: 268736-32-9
2-((2R,3S,5R)-3-methyl-5-{[(1R,2S)-2-phenylcyclohexyl]oxy}tetrahydro-2-furanyl)acetaldehyde

Guidance literature:: Multi-step reaction with 3 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

3.1: 95 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 2.5 h / -78 - 20 °C

With 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; triethyl borane; oxygen; tri-n-butyl-tin hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; toluene; 3.1: Swern oxidation;
DOI:10.1002/chem.200390180

Reference yield:

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

: 268736-32-9
2-((2R,3S,5R)-3-methyl-5-{[(1R,2S)-2-phenylcyclohexyl]oxy}tetrahydro-2-furanyl)acetaldehyde

Guidance literature:: Multi-step reaction with 2 steps

1.1: 9-BBN / tetrahydrofuran / 3 h / Heating

1.2: 93 percent / aq. NaOH; H₂O₂ / tetrahydrofuran / 1 h / 20 °C

2.1: 95 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 2.5 h / -78 - 20 °C

With 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 2.1: Swern oxidation;
DOI:10.1002/chem.200390180