(2R)-3-<(tert-butyldimethylsilyl)oxymethyl>-2-<2-(methoxycarbonyl)-2-phenylselenopropyl>-4-methyl-2,5-dihydrofuran

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Chemical Name:(2R)-3-<(tert-butyldimethylsilyl)oxymethyl>-2-<2-(methoxycarbonyl)-2-phenylselenopropyl>-4-methyl-2,5-dihydrofuran
CAS No.:138945-23-0
Molecular Formula:C₂₃H₃₆O₄SeSi
Molecular Weight:483.582
Hs Code.:

Synonyms:(2R)-3-<(tert-butyldimethylsilyl)oxymethyl>-2-<2-(methoxycarbonyl)-2-phenylselenopropyl>-4-methyl-2,5-dihydrofuran

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Chemical Property of (2R)-3-<(tert-butyldimethylsilyl)oxymethyl>-2-<2-(methoxycarbonyl)-2-phenylselenopropyl>-4-methyl-2,5-dihydrofuran

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Technology Process of (2R)-3-<(tert-butyldimethylsilyl)oxymethyl>-2-<2-(methoxycarbonyl)-2-phenylselenopropyl>-4-methyl-2,5-dihydrofuran

There total 24 articles about (2R)-3-<(tert-butyldimethylsilyl)oxymethyl>-2-<2-(methoxycarbonyl)-2-phenylselenopropyl>-4-methyl-2,5-dihydrofuran 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:

: 138944-97-5,138945-35-4
(1S,2R,5S)-5-(1-hydroxypropan-2-yl)-2-methyl-3-cyclohexenol tetrahydropyranyl ether

: 138945-23-0
(2R)-3-<(tert-butyldimethylsilyl)oxymethyl>-2-<2-(methoxycarbonyl)-2-phenylselenopropyl>-4-methyl-2,5-dihydrofuran

Guidance literature:: Multi-step reaction with 11 steps

1: 60 percent / ethyl acetate / 3 h / -65 °C

2: 30 percent / 10percent H₂SO₄ / acetone / 72 h / 50 °C

3: 70 percent / W₂-Raney nickel / acetone / 7 h / Ambient temperature

4: 89 percent / Jones reagent / acetone / 0.08 h / 0 °C

5: 1) lithium diisopropylamide (from diisopropylamine and n-butyllithium hexane solution at 0 deg C) / 1) THF, -78 deg C, 1 h, 2) -78 deg C, 2 h

6: 1a) O₃, NaHCO₃, 1b) methylsulfide / 1a) aq. CH₂Cl₂, MeOH, -78 deg C, 30 min, 1b) r.t., 1 h, 2) ether

7: 1) piperidine, molecular sieves 3 Angstroem / 1) benzene, r.t., 26 h, 2) THF, -110 deg C, 1 h

8: 28 percent / 80percent m-chloroperbenzoic acid / CH₂Cl₂ / 0.33 h / -78 °C

9: 1) 0.5 M 9-borabicyclo<3.3.1>nonane, 2) 2 N NaOH, 35percent H₂O₂ / 1) THF, r.t., 2 h, 2) 3h

10: 97 percent / imidazole / tetrahydrofuran / 10 h / Ambient temperature

11: 1) lithium diisopropylamide (from diisopropylamine and n-butyllithium hexane solution at -78 deg C), 2) hexamethylphophoric triamide / 1) THF, -78 deg C, 30 min, 2) THF, -78 deg C, 20 min

With piperidine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; jones reagent; methylthiol; 3 A molecular sieve; sulfuric acid; dihydrogen peroxide; sodium hydrogencarbonate; ozone; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; W₂-Raney Nickel; In tetrahydrofuran; dichloromethane; ethyl acetate; acetone;
DOI:10.1248/cpb.39.2514

Reference yield:

: 76339-71-4
(2S,3R,5S)-2-methyl-5-(1-methylethenyl)-3-(phenylseleno)-cyclohexanone

: 138945-23-0
(2R)-3-<(tert-butyldimethylsilyl)oxymethyl>-2-<2-(methoxycarbonyl)-2-phenylselenopropyl>-4-methyl-2,5-dihydrofuran

Guidance literature:: Multi-step reaction with 14 steps

1: 78.5 percent / LiAlH₄ / diethyl ether / 0.08 h / 0 °C

2: 1.02 g / pyridinium p-toluenesulfonate / CH₂Cl₂ / 7 h / Ambient temperature

3: 1) borane-THF complex, 2) 35percent H₂O₂, 3N KOH / 1) THF, -65 deg C, 2) 65 deg C, 15 h

4: 60 percent / ethyl acetate / 3 h / -65 °C

5: 30 percent / 10percent H₂SO₄ / acetone / 72 h / 50 °C

6: 70 percent / W₂-Raney nickel / acetone / 7 h / Ambient temperature

7: 89 percent / Jones reagent / acetone / 0.08 h / 0 °C

8: 1) lithium diisopropylamide (from diisopropylamine and n-butyllithium hexane solution at 0 deg C) / 1) THF, -78 deg C, 1 h, 2) -78 deg C, 2 h

9: 1a) O₃, NaHCO₃, 1b) methylsulfide / 1a) aq. CH₂Cl₂, MeOH, -78 deg C, 30 min, 1b) r.t., 1 h, 2) ether

10: 1) piperidine, molecular sieves 3 Angstroem / 1) benzene, r.t., 26 h, 2) THF, -110 deg C, 1 h

11: 28 percent / 80percent m-chloroperbenzoic acid / CH₂Cl₂ / 0.33 h / -78 °C

12: 1) 0.5 M 9-borabicyclo<3.3.1>nonane, 2) 2 N NaOH, 35percent H₂O₂ / 1) THF, r.t., 2 h, 2) 3h

13: 97 percent / imidazole / tetrahydrofuran / 10 h / Ambient temperature

14: 1) lithium diisopropylamide (from diisopropylamine and n-butyllithium hexane solution at -78 deg C), 2) hexamethylphophoric triamide / 1) THF, -78 deg C, 30 min, 2) THF, -78 deg C, 20 min

With piperidine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; jones reagent; borane-THF; methylthiol; 3 A molecular sieve; sulfuric acid; dihydrogen peroxide; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; ozone; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; W₂-Raney Nickel; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; acetone;
DOI:10.1248/cpb.39.2514

Reference yield:

: 97691-00-4
(1S,2S,3R,5S)-2-methyl-5-(1-methylethenyl)-3-(phenylseleno)-cyclohexanol tetrahydropyranyl ether

: 138945-23-0
(2R)-3-<(tert-butyldimethylsilyl)oxymethyl>-2-<2-(methoxycarbonyl)-2-phenylselenopropyl>-4-methyl-2,5-dihydrofuran

Guidance literature:: Multi-step reaction with 12 steps

1: 1) borane-THF complex, 2) 35percent H₂O₂, 3N KOH / 1) THF, -65 deg C, 2) 65 deg C, 15 h

2: 60 percent / ethyl acetate / 3 h / -65 °C

3: 30 percent / 10percent H₂SO₄ / acetone / 72 h / 50 °C

4: 70 percent / W₂-Raney nickel / acetone / 7 h / Ambient temperature

5: 89 percent / Jones reagent / acetone / 0.08 h / 0 °C

6: 1) lithium diisopropylamide (from diisopropylamine and n-butyllithium hexane solution at 0 deg C) / 1) THF, -78 deg C, 1 h, 2) -78 deg C, 2 h

7: 1a) O₃, NaHCO₃, 1b) methylsulfide / 1a) aq. CH₂Cl₂, MeOH, -78 deg C, 30 min, 1b) r.t., 1 h, 2) ether

8: 1) piperidine, molecular sieves 3 Angstroem / 1) benzene, r.t., 26 h, 2) THF, -110 deg C, 1 h

9: 28 percent / 80percent m-chloroperbenzoic acid / CH₂Cl₂ / 0.33 h / -78 °C

10: 1) 0.5 M 9-borabicyclo<3.3.1>nonane, 2) 2 N NaOH, 35percent H₂O₂ / 1) THF, r.t., 2 h, 2) 3h

11: 97 percent / imidazole / tetrahydrofuran / 10 h / Ambient temperature

12: 1) lithium diisopropylamide (from diisopropylamine and n-butyllithium hexane solution at -78 deg C), 2) hexamethylphophoric triamide / 1) THF, -78 deg C, 30 min, 2) THF, -78 deg C, 20 min

With piperidine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; jones reagent; borane-THF; methylthiol; 3 A molecular sieve; sulfuric acid; dihydrogen peroxide; sodium hydrogencarbonate; ozone; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; W₂-Raney Nickel; In tetrahydrofuran; dichloromethane; ethyl acetate; acetone;
DOI:10.1248/cpb.39.2514