223734-62-1

Basic information

• Product Name: 2-[[(1S)-1-(3-Butyn-1-yl)hexyl]oxy]tetrahydro-2H-pyran
• Synonyms: (S)-5-[(Tetrahydropyranyl)oxy]-1-decyne;2-[[(1S)-1-(3-Butyn-1-yl)hexyl]oxy]tetrahydro-2H-pyran;2-((S)-Dec-1-yn-5-yloxy)tetrahydro-2H-pyran;2H-Pyran, 2-[[(1S)-1-(3-butyn-1-yl)hexyl]oxy]tetrahydro-;2-[(5S)-dec-1-yn-5-yloxy]oxane
• CAS NO: 223734-62-1
• Molecular Formula: C₁₅H₂₆O₂
• Molecular Weight: 238.36574
• Product Categories: Treprostinil
• Mol File: 223734-62-1.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-[[(1S)-1-(3-Butyn-1-yl)hexyl]oxy]tetrahydro-2H-pyran(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[[(1S)-1-(3-Butyn-1-yl)hexyl]oxy]tetrahydro-2H-pyran(223734-62-1)
• EPA Substance Registry System: 2-[[(1S)-1-(3-Butyn-1-yl)hexyl]oxy]tetrahydro-2H-pyran(223734-62-1)

Safety Data

• Hazardous Substances Data: 223734-62-1(Hazardous Substances Data)

Usage

General Description

2-[[(1S)-1-(3-Butyn-1-yl)hexyl]oxy]tetrahydro-2H-pyran is a specific chemical compound with a unique structure that includes a tetrahydropyran ring, which is a six-membered cyclic ether. 2-[[(1S)-1-(3-Butyn-1-yl)hexyl]oxy]tetrahydro-2H-pyran also has a butynyl and a hexyl group attached to it. This chemical compound can be of potential use in fields such as synthetic chemistry, biochemistry, pharmacology, and materials science. However, the specific properties, potential applications, and toxicity of this chemical compound may vary and it could require further research to gain comprehensive knowledge about it.

Synthetic route

1-(trimethylsilyl)-O-tetrahydropyran-2-yl-1-decyn-5-(S)-ol (678992-52-4) → 2-[[(1S)-1-(3-butynyl)hexyl]oxy]tetrahydro-2H-pyran (223734-62-1)

Conditions	Yield
With sodium hydroxide In ethanol at 20℃; for 20h;

3,4-dihydro-2H-pyran (110-87-2) + (+-)-4-hydroxy-3-methyl-butan-2-one → 2-[[(1S)-1-(3-butynyl)hexyl]oxy]tetrahydro-2H-pyran (223734-62-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: TsOH*pyridine / CH2Cl2 / 15 h / 20 °C 2: BuLi / tetrahydrofuran; hexane / 15 h / 0 - 20 °C 3: NaOH / ethanol / 20 h / 20 °C View Scheme

(S)-1-chloroheptane-2-ol (81007-64-9) → 2-[[(1S)-1-(3-butynyl)hexyl]oxy]tetrahydro-2H-pyran (223734-62-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: TsOH*pyridine / CH2Cl2 / 15 h / 20 °C 2: BuLi / tetrahydrofuran; hexane / 15 h / 0 - 20 °C 3: NaOH / ethanol / 20 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1.1: sodium hydroxide / tert-butyl methyl ether / 18 h / 25 °C 2.1: magnesium; iodine; mercury dichloride / diethyl ether / 0 - 36 °C / Inert atmosphere 2.2: 0.5 h 3.1: pyridinium p-toluenesulfonate / dichloromethane / 24 h / 0 - 25 °C View Scheme
Multi-step reaction with 4 steps 1.1: sodium hydroxide / tert-butyl methyl ether / 18 h / 25 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 3.5 h / -50 - -35 °C / Inert atmosphere 2.2: 2.5 h / -40 - -20 °C 3.1: sodium hydroxide; ethanol / 2 h / 25 °C 4.1: pyridinium p-toluenesulfonate / dichloromethane / 24 h / 0 - 25 °C View Scheme
Multi-step reaction with 5 steps 1: sodium hydroxide / tert-butyl methyl ether / 18 h / 25 °C 2: copper(l) iodide / tetrahydrofuran / 3 h / 0 - 5 °C / Inert atmosphere 3: pyridinium p-toluenesulfonate / dichloromethane / 25 °C 4: pyridine; pyridinium perbromide hydrobromide / dichloromethane / 3 h / 0 - 5 °C 5: sodium amide / tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene / Inert atmosphere; Reflux View Scheme

(S)-1-chloro-O-tetrahydropyran-2-yl-heptan-2-ol (678992-51-3) → 2-[[(1S)-1-(3-butynyl)hexyl]oxy]tetrahydro-2H-pyran (223734-62-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: BuLi / tetrahydrofuran; hexane / 15 h / 0 - 20 °C 2: NaOH / ethanol / 20 h / 20 °C View Scheme

(S)-2-pentyloxirane (61229-03-6) → 2-[[(1S)-1-(3-butynyl)hexyl]oxy]tetrahydro-2H-pyran (223734-62-1)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: magnesium; iodine; mercury dichloride / diethyl ether / 0 - 36 °C / Inert atmosphere 1.2: 0.5 h 2.1: pyridinium p-toluenesulfonate / dichloromethane / 24 h / 0 - 25 °C View Scheme
Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 3.5 h / -50 - -35 °C / Inert atmosphere 1.2: 2.5 h / -40 - -20 °C 2.1: sodium hydroxide; ethanol / 2 h / 25 °C 3.1: pyridinium p-toluenesulfonate / dichloromethane / 24 h / 0 - 25 °C View Scheme
Multi-step reaction with 4 steps 1: copper(l) iodide / tetrahydrofuran / 3 h / 0 - 5 °C / Inert atmosphere 2: pyridinium p-toluenesulfonate / dichloromethane / 25 °C 3: pyridine; pyridinium perbromide hydrobromide / dichloromethane / 3 h / 0 - 5 °C 4: sodium amide / tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene / Inert atmosphere; Reflux View Scheme

(5S)-dec-1-en-5-ol (1374332-11-2) → 2-[[(1S)-1-(3-butynyl)hexyl]oxy]tetrahydro-2H-pyran (223734-62-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: pyridinium p-toluenesulfonate / dichloromethane / 25 °C 2: pyridine; pyridinium perbromide hydrobromide / dichloromethane / 3 h / 0 - 5 °C 3: sodium amide / tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene / Inert atmosphere; Reflux View Scheme

3,4-dihydro-2H-pyran (110-87-2) + (S)-Dec-1-yn-5-ol (848609-05-2) → 2-[[(1S)-1-(3-butynyl)hexyl]oxy]tetrahydro-2H-pyran (223734-62-1)

Conditions	Yield
With pyridinium p-toluenesulfonate In dichloromethane at 0 - 25℃; for 24h; Temperature;	65.1 g

C15H28O2 → 2-[[(1S)-1-(3-butynyl)hexyl]oxy]tetrahydro-2H-pyran (223734-62-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine; pyridinium perbromide hydrobromide / dichloromethane / 3 h / 0 - 5 °C 2: sodium amide / tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene / Inert atmosphere; Reflux View Scheme

C15H28Br2O2 → 2-[[(1S)-1-(3-butynyl)hexyl]oxy]tetrahydro-2H-pyran (223734-62-1)

Conditions	Yield
With sodium amide In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene Inert atmosphere; Reflux;

C13H26OSi → 2-[[(1S)-1-(3-butynyl)hexyl]oxy]tetrahydro-2H-pyran (223734-62-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide; ethanol / 2 h / 25 °C 2: pyridinium p-toluenesulfonate / dichloromethane / 24 h / 0 - 25 °C View Scheme

2-allyl-3-methoxybenzaldehyde (94956-98-6) + 2-[[(1S)-1-(3-butynyl)hexyl]oxy]tetrahydro-2H-pyran (223734-62-1) → 3-methoxy-2-(2-propenyl)-α-[(5S)-5-[(tetrahydro-2H-pyran-2-yl)oxy]-1-decynyl]benzenemethanol (223734-56-3)

Conditions	Yield
With ethylmagnesium bromide In tetrahydrofuran; diethyl ether at 0 - 20℃;	92%

2-allyl-3-methoxybenzaldehyde (94956-98-6) + 2-[[(1S)-1-(3-butynyl)hexyl]oxy]tetrahydro-2H-pyran (223734-62-1) → (αS)-3-methoxy-2-(2-propenyl)-α-[(5S)-5-[(tetrahydro-2H-pyran-2-yl)oxy]-1-decynyl]benzenemethanol (223734-58-5)

Conditions	Yield
Stage #1: 2-[[(1S)-1-(3-butynyl)hexyl]oxy]tetrahydro-2H-pyran With (1S,2R)-(+)-N-methylephedrine; zinc trifluoromethanesulfonate; triethylamine In toluene at 20℃; for 0.25h; Stage #2: 2-allyl-3-methoxybenzaldehyde In toluene for 3h;	87%

2-allyl-3-(carbomethoxy)benzyloxybenzaldehyde (1351472-15-5) + 2-[[(1S)-1-(3-butynyl)hexyl]oxy]tetrahydro-2H-pyran (223734-62-1) → C34H44O6 (1351472-16-6)

Conditions	Yield
Stage #1: 2-[[(1S)-1-(3-butynyl)hexyl]oxy]tetrahydro-2H-pyran With (1S,2R)-(+)-N-methylephedrine; zinc trifluoromethanesulfonate; triethylamine In toluene at 20℃; Stage #2: 2-allyl-3-(carbomethoxy)benzyloxybenzaldehyde In toluene at 20℃; for 2h;	84%

2-allyl-3-benzyloxy-N-methoxy-N-methyl-benzamide + 2-[[(1S)-1-(3-butynyl)hexyl]oxy]tetrahydro-2H-pyran (223734-62-1) → (6S)-1-(2-allyl-3-(benzyloxy)phenyl)-6-((tetrahydro-2H-pyran-2-yl)oxy)undec-2-yn-1-one

Conditions	Yield
Stage #1: 2-[[(1S)-1-(3-butynyl)hexyl]oxy]tetrahydro-2H-pyran With ethylmagnesium bromide In tetrahydrofuran; diethyl ether at 35 - 40℃; Stage #2: 2-allyl-3-benzyloxy-N-methoxy-N-methyl-benzamide In tetrahydrofuran; diethyl ether at 25℃; for 1h; Reflux;	77.9%

2-allyl-3-[(carbomethoxy)methoxy]benzaldehyde (1292809-43-8) + 2-[[(1S)-1-(3-butynyl)hexyl]oxy]tetrahydro-2H-pyran (223734-62-1) → C28H40O6 (1351472-11-1)

Conditions	Yield
Stage #1: 2-[[(1S)-1-(3-butynyl)hexyl]oxy]tetrahydro-2H-pyran With (1S,2R)-(+)-N-methylephedrine; zinc trifluoromethanesulfonate; triethylamine In toluene at 20℃; Stage #2: 2-allyl-3-[(carbomethoxy)methoxy]benzaldehyde In toluene at 20℃; for 16h;	70%

2-[[(1S)-1-(3-butynyl)hexyl]oxy]tetrahydro-2H-pyran (223734-62-1) → treprostinil (81846-19-7)

Conditions

Yield

Multi-step reaction with 11 steps 1: 92 percent / EtMgBr / tetrahydrofuran; diethyl ether / 0 - 20 °C 2: 75 percent / PCC / CH2Cl2 / 15 h / 0 - 20 °C 3: BH3; Me2S; (R)-methyloxazaborolidine / toluene; tetrahydrofuran / 1 h / -30 °C 4: 92 percent / imidazole; 4-(dimethylamino)pyridine / dimethylformamide; CH2Cl2 / 15 h / 20 °C 5: CH2Cl2 / 2 h / 20 °C 6: H2; K2CO3 / Pd/C / ethanol / 20 °C / 4654.33 Torr 7: NaBH4; aq. NaOH / ethanol / 6 h / -10 °C 8: 2162 g / TsOH / methanol / 15 h / 0 - 20 °C 9: 80 percent / Ph2PH; n-BuLi / tetrahydrofuran; hexane / 20 h / Heating 10: 100 percent / K2CO3; tetrabutylammonium bromide / acetone / 8 h / Heating 11: 83 percent / aq. KOH / methanol / 3 h / Heating View Scheme

2-[[(1S)-1-(3-butynyl)hexyl]oxy]tetrahydro-2H-pyran (223734-62-1) → (1R,2R,3aS,9aS)-1-[(3S)-3-hydroxyoctyl]-5-methoxy-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalen-2-ol (101692-01-7)

Conditions

Yield

Multi-step reaction with 8 steps 1: 92 percent / EtMgBr / tetrahydrofuran; diethyl ether / 0 - 20 °C 2: 75 percent / PCC / CH2Cl2 / 15 h / 0 - 20 °C 3: BH3; Me2S; (R)-methyloxazaborolidine / toluene; tetrahydrofuran / 1 h / -30 °C 4: 92 percent / imidazole; 4-(dimethylamino)pyridine / dimethylformamide; CH2Cl2 / 15 h / 20 °C 5: CH2Cl2 / 2 h / 20 °C 6: H2; K2CO3 / Pd/C / ethanol / 20 °C / 4654.33 Torr 7: NaBH4; aq. NaOH / ethanol / 6 h / -10 °C 8: 2162 g / TsOH / methanol / 15 h / 0 - 20 °C View Scheme

2-[[(1S)-1-(3-butynyl)hexyl]oxy]tetrahydro-2H-pyran (223734-62-1) → (1R,2R,3aS,9aS)-1-((S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-2,5-diol (101692-02-8)

Conditions

Yield

Multi-step reaction with 9 steps 1: 92 percent / EtMgBr / tetrahydrofuran; diethyl ether / 0 - 20 °C 2: 75 percent / PCC / CH2Cl2 / 15 h / 0 - 20 °C 3: BH3; Me2S; (R)-methyloxazaborolidine / toluene; tetrahydrofuran / 1 h / -30 °C 4: 92 percent / imidazole; 4-(dimethylamino)pyridine / dimethylformamide; CH2Cl2 / 15 h / 20 °C 5: CH2Cl2 / 2 h / 20 °C 6: H2; K2CO3 / Pd/C / ethanol / 20 °C / 4654.33 Torr 7: NaBH4; aq. NaOH / ethanol / 6 h / -10 °C 8: 2162 g / TsOH / methanol / 15 h / 0 - 20 °C 9: 80 percent / Ph2PH; n-BuLi / tetrahydrofuran; hexane / 20 h / Heating View Scheme

2-[[(1S)-1-(3-butynyl)hexyl]oxy]tetrahydro-2H-pyran (223734-62-1) → 2-((1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-2-hydroxy-1-((3S)-3-hydroxyoctyl)-1H-cyclopenta[b]naphthalen-5-yloxy)acetonitrile (101692-03-9)

Conditions

Yield

Multi-step reaction with 10 steps 1: 92 percent / EtMgBr / tetrahydrofuran; diethyl ether / 0 - 20 °C 2: 75 percent / PCC / CH2Cl2 / 15 h / 0 - 20 °C 3: BH3; Me2S; (R)-methyloxazaborolidine / toluene; tetrahydrofuran / 1 h / -30 °C 4: 92 percent / imidazole; 4-(dimethylamino)pyridine / dimethylformamide; CH2Cl2 / 15 h / 20 °C 5: CH2Cl2 / 2 h / 20 °C 6: H2; K2CO3 / Pd/C / ethanol / 20 °C / 4654.33 Torr 7: NaBH4; aq. NaOH / ethanol / 6 h / -10 °C 8: 2162 g / TsOH / methanol / 15 h / 0 - 20 °C 9: 80 percent / Ph2PH; n-BuLi / tetrahydrofuran; hexane / 20 h / Heating 10: 100 percent / K2CO3; tetrabutylammonium bromide / acetone / 8 h / Heating View Scheme

2-[[(1S)-1-(3-butynyl)hexyl]oxy]tetrahydro-2H-pyran (223734-62-1) → (6S)-1-[3-methoxy-2-(2-propenyl)phenyl]-6-[(tetrahydro-2H-pyran-2-yl)oxy]-2-undecyn-1-one (223734-57-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 92 percent / EtMgBr / tetrahydrofuran; diethyl ether / 0 - 20 °C 2: 75 percent / PCC / CH2Cl2 / 15 h / 0 - 20 °C View Scheme

2-[[(1S)-1-(3-butynyl)hexyl]oxy]tetrahydro-2H-pyran (223734-62-1) → (αS)-3-methoxy-2-(2-propenyl)-α-[(5S)-5-[(tetrahydro-2H-pyran-2-yl)oxy]-1-decynyl]benzenemethanol (223734-58-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 92 percent / EtMgBr / tetrahydrofuran; diethyl ether / 0 - 20 °C 2: 75 percent / PCC / CH2Cl2 / 15 h / 0 - 20 °C 3: BH3; Me2S; (R)-methyloxazaborolidine / toluene; tetrahydrofuran / 1 h / -30 °C View Scheme

2-[[(1S)-1-(3-butynyl)hexyl]oxy]tetrahydro-2H-pyran (223734-62-1) → 1,3,3a,4,9,9a-hexahydro-5-methoxy-1-[(3S)-3-[(tetrahydro-2H-pyran-2-yl)oxy]octyl]-2H-benz[f]inden-2-one (223734-61-0)

Conditions

Yield

Multi-step reaction with 6 steps 1: 92 percent / EtMgBr / tetrahydrofuran; diethyl ether / 0 - 20 °C 2: 75 percent / PCC / CH2Cl2 / 15 h / 0 - 20 °C 3: BH3; Me2S; (R)-methyloxazaborolidine / toluene; tetrahydrofuran / 1 h / -30 °C 4: 92 percent / imidazole; 4-(dimethylamino)pyridine / dimethylformamide; CH2Cl2 / 15 h / 20 °C 5: CH2Cl2 / 2 h / 20 °C 6: H2; K2CO3 / Pd/C / ethanol / 20 °C / 4654.33 Torr View Scheme

2-[[(1S)-1-(3-butynyl)hexyl]oxy]tetrahydro-2H-pyran (223734-62-1) → (1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-5-methoxy-1-[(3S)-3-[(tetrahydro-2H-pyran-2-yl)oxy]octyl]-1H-benz[f]inden-2-ol (101758-87-6)

Conditions

Yield

Multi-step reaction with 7 steps 1: 92 percent / EtMgBr / tetrahydrofuran; diethyl ether / 0 - 20 °C 2: 75 percent / PCC / CH2Cl2 / 15 h / 0 - 20 °C 3: BH3; Me2S; (R)-methyloxazaborolidine / toluene; tetrahydrofuran / 1 h / -30 °C 4: 92 percent / imidazole; 4-(dimethylamino)pyridine / dimethylformamide; CH2Cl2 / 15 h / 20 °C 5: CH2Cl2 / 2 h / 20 °C 6: H2; K2CO3 / Pd/C / ethanol / 20 °C / 4654.33 Torr 7: NaBH4; aq. NaOH / ethanol / 6 h / -10 °C View Scheme

2-[[(1S)-1-(3-butynyl)hexyl]oxy]tetrahydro-2H-pyran (223734-62-1) → (1,1-dimethylethyl)[[(1S,6S)-1-[3-methoxy-2-(2-propenyl)phenyl]-6-[(tetrahydro-2H-pyran-2-yl)oxy]-2-undecynyl]oxy]dimethylsilane (223734-59-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: 92 percent / EtMgBr / tetrahydrofuran; diethyl ether / 0 - 20 °C 2: 75 percent / PCC / CH2Cl2 / 15 h / 0 - 20 °C 3: BH3; Me2S; (R)-methyloxazaborolidine / toluene; tetrahydrofuran / 1 h / -30 °C 4: 92 percent / imidazole; 4-(dimethylamino)pyridine / dimethylformamide; CH2Cl2 / 15 h / 20 °C View Scheme

2-[[(1S)-1-(3-butynyl)hexyl]oxy]tetrahydro-2H-pyran (223734-62-1) → (3aS,9aS)-9-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3,3a,4,9-tetrahydro-5-methoxy-1-[(3S)-3-[(tetrahydro-2H-pyran-2-yl)oxy]octyl]-2H-benz[f]inden-2-one (223734-60-9)

Conditions	Yield
Multi-step reaction with 5 steps 1: 92 percent / EtMgBr / tetrahydrofuran; diethyl ether / 0 - 20 °C 2: 75 percent / PCC / CH2Cl2 / 15 h / 0 - 20 °C 3: BH3; Me2S; (R)-methyloxazaborolidine / toluene; tetrahydrofuran / 1 h / -30 °C 4: 92 percent / imidazole; 4-(dimethylamino)pyridine / dimethylformamide; CH2Cl2 / 15 h / 20 °C 5: CH2Cl2 / 2 h / 20 °C View Scheme

2-[[(1S)-1-(3-butynyl)hexyl]oxy]tetrahydro-2H-pyran (223734-62-1) → C38H56O4Si

Conditions	Yield
Multi-step reaction with 2 steps 1: zinc trifluoromethanesulfonate; triethylamine; (1S,2R)-(+)-N-methylephedrine 2: 1H-imidazole / dichloromethane View Scheme

2-[[(1S)-1-(3-butynyl)hexyl]oxy]tetrahydro-2H-pyran (223734-62-1) → C39H56O5Si

Conditions	Yield
Multi-step reaction with 3 steps 1: zinc trifluoromethanesulfonate; triethylamine; (1S,2R)-(+)-N-methylephedrine 2: 1H-imidazole / dichloromethane 3: Co(CO)8 / 1,2-dimethoxyethane / 3620.13 Torr View Scheme

2-[[(1S)-1-(3-butynyl)hexyl]oxy]tetrahydro-2H-pyran (223734-62-1) → C26H38O4

Conditions	Yield
Multi-step reaction with 4 steps 1: zinc trifluoromethanesulfonate; triethylamine; (1S,2R)-(+)-N-methylephedrine 2: 1H-imidazole / dichloromethane 3: Co(CO)8 / 1,2-dimethoxyethane / 3620.13 Torr 4: palladium on activated charcoal; hydrogen; potassium carbonate / ethanol / 4137.29 Torr View Scheme

2-[[(1S)-1-(3-butynyl)hexyl]oxy]tetrahydro-2H-pyran (223734-62-1) → C26H40O4

Conditions	Yield
Multi-step reaction with 5 steps 1: zinc trifluoromethanesulfonate; triethylamine; (1S,2R)-(+)-N-methylephedrine 2: 1H-imidazole / dichloromethane 3: Co(CO)8 / 1,2-dimethoxyethane / 3620.13 Torr 4: palladium on activated charcoal; hydrogen; potassium carbonate / ethanol / 4137.29 Torr 5: sodium hydroxide; sodium tetrahydroborate View Scheme

3-benzyloxy-2-allylbenzaldehyde + 2-[[(1S)-1-(3-butynyl)hexyl]oxy]tetrahydro-2H-pyran (223734-62-1) → C32H42O4

Conditions	Yield
With (1S,2R)-(+)-N-methylephedrine; zinc trifluoromethanesulfonate; triethylamine

Upstream product

• 110-87-2 3,4-dihydro-2H-pyran 
• 848609-05-2 (S)-Dec-1-yn-5-ol 
• 1374332-11-2 (5S)-dec-1-en-5-ol 
• 61229-03-6 (S)-2-pentyloxirane 
• 678992-51-3 (S)-1-chloro-O-tetrahydropyran-2-yl-heptan-2-ol 
• 81007-64-9 (S)-1-chloroheptane-2-ol 
• 678992-52-4 1-(trimethylsilyl)-O-tetrahydropyran-2-yl-1-decyn-5-(S)-ol 

Downstream Products

• 1351472-16-6 C₃₄H₄₄O₆ 
• 1351472-11-1 C₂₈H₄₀O₆ 
• 223734-58-5 (αS)-3-methoxy-2-(2-propenyl)-α-[(5S)-5-[(tetrahydro-2H-pyran-2-yl)oxy]-1-decynyl]benzenemethanol 
• 223734-59-6 (1,1-dimethylethyl)[[(1S,6S)-1-[3-methoxy-2-(2-propenyl)phenyl]-6-[(tetrahydro-2H-pyran-2-yl)oxy]-2-undecynyl]oxy]dimethylsilane 
• 223734-57-4 (6S)-1-[3-methoxy-2-(2-propenyl)phenyl]-6-[(tetrahydro-2H-pyran-2-yl)oxy]-2-undecyn-1-one 
• 101692-02-8 (1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-1-((S)-3-hydroxyoctyl)-1H-cyclopenta[b]naphthalene-2,5-diol 
• 81846-19-7 treprostinil 
• 223734-56-3 3-methoxy-2-(2-propenyl)-α-[(5S)-5-[(tetrahydro-2H-pyran-2-yl)oxy]-1-decynyl]benzenemethanol 

Relevant articles and documents

The curved front row neil intermediate preparation method

The invention relates to a preparation method for a treprostinil intermediate (I). The preparation method comprises the steps that: a compound of a formula (II) and a compound of a formula (III) or acidic salt thereof react in the presence of a condensing agent to obtain a compound of a formula (IV); the compound of the formula (IV) and a compound of a formula (V) react to obtain a compound of a formula (I). According to the preparation method for the treprostinil intermediate, weinreb amide and alkyne negative ions react to directly obtain a ketone compound (I), so that environment pollution caused by heavy metal (a PCC oxidant) is avoided, and the adoption of a butyl lithium low-temperature reaction method is also avoided. The preparation method for the treprostinil intermediate has the advantages that reaction conditions are mild, the yield is high, the purity of products is high, and the industrial application prospect is wide. (Formulae (I), (II), (III), (IV) and (V) are shown in the specification)