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[ CAS No. 51450-44-3 ] {[proInfo.proName]}

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Chemical Structure| 51450-44-3
Chemical Structure| 51450-44-3
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Product Details of [ 51450-44-3 ]

CAS No. :51450-44-3 MDL No. :MFCD22681529
Formula : C6H12O2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 116.16 Pubchem ID :-
Synonyms :

Safety of [ 51450-44-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P210-P305+P351+P338 UN#:N/A
Hazard Statements:H227-H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 51450-44-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 51450-44-3 ]

[ 51450-44-3 ] Synthesis Path-Downstream   1~38

  • 1
  • C21H36O2Si [ No CAS ]
  • [ 51450-44-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 2.1: triphenylphosphine gold (I) chloride; silver trifluoromethanesulfonate / dichloromethane / 0.58 h / 20 °C / Molecular sieve; Inert atmosphere 3.1: ozone / methanol; dichloromethane / 0.5 h / -78 °C 3.2: 0 - 20 °C
  • 2
  • [ 1268368-57-5 ]
  • [ 51450-44-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: triphenylphosphine gold (I) chloride; silver trifluoromethanesulfonate / dichloromethane / 0.58 h / 20 °C / Molecular sieve; Inert atmosphere 2.1: ozone / methanol; dichloromethane / 0.5 h / -78 °C 2.2: 0 - 20 °C
  • 3
  • [ 1268368-69-9 ]
  • [ 51450-44-3 ]
YieldReaction ConditionsOperation in experiment
48% Stage #1: (S,E)-2-(4-phenylbut-1-en-1-yl)tetrahydro-2H-pyran With ozone In methanol; dichloromethane at -78℃; for 0.5h; Stage #2: With sodium tetrahydroborate In methanol; dichloromethane at 0 - 20℃;
  • 4
  • [ 1268368-80-4 ]
  • [ 51450-44-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: (1S,2S)-(+)-N-tosyl-1,2-diphenylethane-1,2-diamine[η6-1-isopropyl-4-methylbenzene]-ruthenium(II); tetrabutyl-ammonium chloride; sodium formate / dichloromethane; water / 20 h / 20 °C / Inert atmosphere; Large scale reaction 2.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 20 h / 0 °C / Inert atmosphere 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 4.1: triphenylphosphine gold (I) chloride; silver trifluoromethanesulfonate / dichloromethane / 0.58 h / 20 °C / Molecular sieve; Inert atmosphere 5.1: ozone / methanol; dichloromethane / 0.5 h / -78 °C 5.2: 0 - 20 °C
  • 5
  • [ 1268368-81-5 ]
  • [ 51450-44-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 20 h / 0 °C / Inert atmosphere 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 3.1: triphenylphosphine gold (I) chloride; silver trifluoromethanesulfonate / dichloromethane / 0.58 h / 20 °C / Molecular sieve; Inert atmosphere 4.1: ozone / methanol; dichloromethane / 0.5 h / -78 °C 4.2: 0 - 20 °C
  • 6
  • [ 73448-13-2 ]
  • [ 51450-44-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.92 h / -78 °C / Inert atmosphere 1.2: -78 - 20 °C / Inert atmosphere 2.1: (1S,2S)-(+)-N-tosyl-1,2-diphenylethane-1,2-diamine[η6-1-isopropyl-4-methylbenzene]-ruthenium(II); tetrabutyl-ammonium chloride; sodium formate / dichloromethane; water / 20 h / 20 °C / Inert atmosphere; Large scale reaction 3.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 20 h / 0 °C / Inert atmosphere 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 5.1: triphenylphosphine gold (I) chloride; silver trifluoromethanesulfonate / dichloromethane / 0.58 h / 20 °C / Molecular sieve; Inert atmosphere 6.1: ozone / methanol; dichloromethane / 0.5 h / -78 °C 6.2: 0 - 20 °C
  • 7
  • [ 51450-44-3 ]
  • [ 58479-61-1 ]
  • [ 913636-40-5 ]
YieldReaction ConditionsOperation in experiment
98% With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; for 12h; Inert atmosphere;
  • 8
  • [ 51450-44-3 ]
  • [ 58479-61-1 ]
  • [ 1449679-36-0 ]
  • [ 161561-86-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1H-imidazole / N,N-dimethyl-formamide / 12 h / 0 - 20 °C / Inert atmosphere 2: dipyridinium dichromate / 1,2-dichloro-ethane / 4 h / Inert atmosphere; Molecular sieve; Reflux
  • 9
  • [ 51450-44-3 ]
  • ({(2S)-6-[3-(1,4-dioxaspiro[4.5]decan-2-yl)propylidene]tetrahydro-2H-pyran-2-yl}methoxy)(tert-butyl)diphenylsilane [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: 1H-imidazole / N,N-dimethyl-formamide / 12 h / 0 - 20 °C / Inert atmosphere 2.1: dipyridinium dichromate / 1,2-dichloro-ethane / 4 h / Inert atmosphere; Molecular sieve; Reflux 3.1: hydrogen; palladium 10% on activated carbon / ethyl acetate / 24 h / Inert atmosphere 4.1: boron trifluoride diethyl etherate; lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 20 °C / Inert atmosphere 4.2: 0.67 h / 20 °C / Inert atmosphere
  • 10
  • [ 51450-44-3 ]
  • [ 1430851-97-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: 1H-imidazole / N,N-dimethyl-formamide / 12 h / 0 - 20 °C / Inert atmosphere 2.1: dipyridinium dichromate / 1,2-dichloro-ethane / 4 h / Inert atmosphere; Molecular sieve; Reflux 3.1: hydrogen; palladium 10% on activated carbon / ethyl acetate / 24 h / Inert atmosphere 4.1: boron trifluoride diethyl etherate; lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 20 °C / Inert atmosphere 4.2: 0.67 h / 20 °C / Inert atmosphere 5.1: toluene-4-sulfonic acid / dichloromethane / 0.42 h / 20 °C / Inert atmosphere
  • 11
  • [ 51450-44-3 ]
  • [ 161561-86-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1H-imidazole / N,N-dimethyl-formamide / 12 h / 0 - 20 °C / Inert atmosphere 2: dipyridinium dichromate / 1,2-dichloro-ethane / 4 h / Inert atmosphere; Molecular sieve; Reflux
  • 12
  • [ 51450-44-3 ]
  • [ 175398-31-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 1H-imidazole / N,N-dimethyl-formamide / 12 h / 0 - 20 °C / Inert atmosphere 2: dipyridinium dichromate / 1,2-dichloro-ethane / 4 h / Inert atmosphere; Molecular sieve; Reflux 3: hydrogen; palladium 10% on activated carbon / ethyl acetate / 24 h / Inert atmosphere
  • 13
  • (S)-2-[(benzyloxy)methyl]tetrahydro-2H-pyran [ No CAS ]
  • [ 51450-44-3 ]
YieldReaction ConditionsOperation in experiment
86% With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; 78.2C (2S)-Tetrahydro-2H -pyran-2-ylmethanol [1968] 3.51 g (3.30 mmol) of palladium on carbon (10%)were added to a solution of 17.0 g (82.4 mmol) of (S)-2-[(benzyloxy)methyl]tetrahydro-2H-pyran (96% ee, purity96%) in 120 ml of ethanol, and the mixture was hydrogenatedat room temperature and under standard pressure overnight.Another 1.75 g (1.65 mmol) of palladium on carbon (10%)were then added, and the mixture was hydrogenated at roomtemperature for a further 72 h. Subsequently, the reactionmixture was filtered through Celite and the filtrate was concentrated.The residue was purified chromatographically(silica, dichloromethane/methanol gradient) and the productfractions were freed from the solvent at 50mbar. Yield: 8.23 g (86% of theory)[1969] Optical rotation: [ a]58920.0 =9.1 o (c 0.36 g/100 cm3,CHCI3 ), cf. A. Aponick, B. Biannic, Org. Lett. 2011, 13,1330-1333.[1970] GC/MS [Method 7]: R,=l.82 min; MS: m/z=116(Mt[1971] 1H-NMR (400 MHz, DMSO-d6): o [ppm]=4.51 (t,lH), 3.87-3.81 (m, lH), 3.37-3.18 (m, 4H), 1.80-1.71 (m,lH), 1.59-1.50 (m, lH), 1.49-1.36 (m, 3H), 1.19-1.05 (m,lH).
86% With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; 7.1C (25)-Tetrahydro-2H-pyran-2-ylmethanol 3.51 g (3.30 mmol) of palladium on carbon (10%) were added to a solution of 17.0 g (82.4 mmol) of (S)-2- [(benzyloxy)methyl]tetrahydro-2H-pyran (96% cc, purity 96%) in 120 ml of ethanol, and the mixture was hydrogenated at room temperature and under standard pressure overnight. Another 1.75 g (1.65 mmol) of palladium on carbon (10%) were then added, and the mixture was hydrogenated at room temperature for a further 72 h. Subsequently, the reaction mixture was filtered through Celite and the filtrate was concentrated. The residue was purified chromatographically (silica, dichloromethane/methanol gradient) and the product fractions were freed from the solvent at 50 mbat Yield: 8.23 g (86% of theory)j0710] optical rotation: [a]58920°=+9.1° (c 0.36 g/100 cm3, chloroform), cf. A. Aponick, 8. Biannic, Org. Lett. 2011, 13, 1330-1333.j0711] GC/MS [Method 7]: R=1.82 mm; MS: mlz=116j0712] ‘H-NMR (400 MHz, DMSO-d5): ö [ppm]=4.51 (t, 1H), 3.87-3.81 (m, 1H), 3.37-3.18 (m, 4H), 1.80-1.71 (m, 1H), 1.59-1.50 (m, 1H), 1.49-1.36 (m, 3H), 1.19-1.05 (m, 1H).
86% With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; for 72h; 3.3C (25)-Tetrahydro-2H-pyran-2-ylmethanol 3.51 g (3.30 mmol) of palladium on carbon (10%) were added to a solution of 17.0 g (82.4 mmol)of (S)-2-[(benzyloxy)methyl]tetrahydro-2H-pyran (96% cc, purity 96%) in 120 ml of ethanol, andthe mixture was hydrogenated at room temperature and under standard pressure overnight. Another1.75 g (1.65 mmol) of palladium on carbon (10%) were then added, and the mixture washydrogenated at room temperature for a further 72 h. Subsequently, the reaction mixture was filtered through Celite and the filtrate was concentrated. The residue was purified chromatographically (silica, dichloromethane/methanol gradient) and the product fractions were freed from the solvent at 50 mbar. Yield: 8.23 g (86% of theory)optical rotation: [r]5x92° = + 9.1° (c 0.36 g/100 cm3, chloroform), cf. A. Aponick, B. Biannic, Org.Lett. 2011, 13, 1330-1333.GC/MS [Method 7]: R= 1.82 mm; MS: mlz= 116 (M), ‘H-NMR (400 MHz, DMSO-d6): ö [ppm] = 4.51 (t, 1H), 3.87-3.81 (m, 1H), 3.37-3.18 (m, 4H), 1.80-1.71 (m, 1H), 1.59-1.50 (m, 1H), 1.49-1.36 (m, 3H), 1.19-1.05 (m, 1H).
86% With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; 14.1.D (25)-Tetrahydro-2H-pyran-2-ylmethanol Example 14.1D (25)-Tetrahydro-2H-pyran-2-ylmethanol To a solution of 17.0 g (82.4 mmol) of (S)-2-[(benzyloxy)methyl]tetrahydro-2H-pyran (96% ee, 96% purity) in 120 ml of ethanol were added 3.51 g (3.30 mmol) of palladium on carbon (10%), and hydrogenation was effected at room temperature and under standard pressure overnight. Another 1.75 g (1.65 mmol) of palladium on carbon (10%) were then added, and hydrogenation was effected at room temperature for a further 72 h. Subsequently, the reaction mixture was filtered through Celite and the filtrate was concentrated. The residue was purified by chromatography (silica, dichloromethane/methanol gradient) and the product fractions were freed of the solvent at <25° C. and >50 mbar. Yield: 8.23 g (86% of theory) Optical rotation: [α]58920.0=+9.1° (c 0.36 g/100 cm3, chloroform), cf. A. Aponick, B. Biannic, Org. Lett. 2011, 13, 1330-1333. GC/MS [Method 7]: Rt=1.82 min; MS: m/z=116 (M)+, 1H-NMR (400 MHz, DMSO-d6): δ [ppm]=4.51 (t, 1H), 3.87-3.81 (m, 1H), 3.37-3.18 (m, 4H), 1.80-1.71 (m, 1H), 1.59-1.50 (m, 1H), 1.49-1.36 (m, 3H), 1.19-1.05 (m, 1H).
86% With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; 14.1D (2S)-Tetrahydro-2H-pyran-2-ylmethanol {0707] To a solution of 17.0 g (82.4 mmol) of (S)-2-[(benzyloxy)methyl]tetrahydro-2H-pyran (96% ee, 96% purity) in 120 ml of ethanol were added 3.51 g (3.30 mmol) of palladium on carbon (10%), and hydrogenation was effected at room temperature and under standard pressure overnight. Another 1.75 g (1.65 mmol) of palladium on carbon (10%) were then added, and hydrogenation was effected at room temperature for a further 72 h. Subsequently, the reaction mixture was filtered through Celite and the filtrate was concentrated. The residue was purified by chromatography (silica, dichloromethane/methanol gradient) and the product fractions were freed of the solvent at <25° C. and >50 mbar. Yield: 8.23 g (86% of theory) Optical rotation: [α]58920.0=+9.1° (c 0.36 g/100 cm3, chloroform), cf. A. Aponick, B. Biannic, Org. Lett. 2011, 13, 1330-1333. GC/MS [Method 7]: Rt=1.82 min; MS: m/z=116 (M)+, 1H-NMR (400 MHz, DMSO-d6): δ [ppm]=4.51 (t, 1H), 3.87-3.81 (m, 1H), 3.37-3.18 (m, 4H), 1.80-1.71 (m, 1H), 1.59-1.50 (m, 1H), 1.49-1.36 (m, 3H), 1.19-1.05 (m, 1H).
86% With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; 2.1C (2S)-Tetrahydro-2H-pyran-2-ylmethanol To a solution of 17.0 g (82.4 mmol) of (S)-2-[(benzyloxy)methyl]tetrahydro-2H-pyran (96% ee, 96% purity) in 120 ml of ethanol were added 3.51 g (3.30 mmol) of palladium on carbon (10%), and hydrogenation was effected at room temperature and under standard pressure overnight. Another 1.75 g (1.65 mmol) of palladium on carbon (10%) were then added, and hydrogenation was effected at room temperature for a further 72 h. Subsequently, the reaction mixture was filtered through Celite and the filtrate was concentrated. The residue was purified by chromatography (silica, dichloromethane/methanol gradient) and the product fractions were freed of the solvent at <25° C. and >50 mbar. Yield: 8.23 g (86% of theory) Optical rotation: [α]58920.0=+9.1° (c 0.36 g/100 cm3, chloroform), cf. A. Aponick, B. Biannic, Org. Lett. 2011, 13, 1330-1333. GC/MS [Method 7]: Rt=1.82 min; MS: m/z=116 (M)+, 1H-NMR (400 MHz, DMSO-d6): δ [ppm]=4.51 (t, 1H), 3.87-3.81 (m, 1H), 3.37-3.18 (m, 4H), 1.80-1.71 (m, 1H), 1.59-1.50 (m, 1H), 1.49-1.36 (m, 3H), 1.19-1.05 (m, 1H).
8.23 g With palladium 10% on activated carbon; hydrogen In ethanol at 0℃; 78.2C (2S)-Tetrahydro-2H-pyran-2-ylmethanol 3.51 g (3.30 mmol) of palladium on carbon (10%) wereadded to a solution of 17.0 g (82.4 mmol) of(S)-2-[(benzyloxy)methyl]tetrahydro-2H-pyran (96% ee, purity 96%) in 120 ml ofethanol, and the mixture was hydrogenated at room temperature and understandard pressure overnight. Another 1.75 g (1.65 mmol) of palladium on carbon(10%) were then added, and the mixture was hydrogenated at room temperature fora further 72 h. Subsequently, the reaction mixture was filtered through Celite andthe filtrate was concentrated. The residue was purified chromatographically(silica, dichloromethane/methanol gradient) and the product fractions werefreed from the solvent at 50 mbar. Yield: 8.23 g (86% oftheory)

  • 14
  • rac-2-[(benzyloxy)methyl]tetrahydro-2H-pyran [ No CAS ]
  • [ 51450-44-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: OD-H column / isopropyl alcohol; 2-Methylpentane / 25 °C / Resolution of racemate 2: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C
Multi-step reaction with 2 steps 1: Column: OD-H / 2-Methylpentane; isopropyl alcohol / 25 °C / Resolution of racemate 2: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C / 760.05 Torr
Multi-step reaction with 2 steps 1: column: OD-H 5 μm 250 mm x 20 mm / 2-Methylpentane; isopropyl alcohol / 25 °C 2: palladium 10% on activated carbon; hydrogen / ethanol / 72 h / 20 °C
Multi-step reaction with 2 steps 1: OD-H / isopropyl alcohol; 2-Methylpentane / 25 °C / Resolution of racemate 2: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C
Multi-step reaction with 2 steps 1: OD-H 5 μm 250mmx20 mm / 2-Methylpentane; isopropyl alcohol / 25 °C / Resolution of racemate 2: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C / 760.05 Torr
Multi-step reaction with 2 steps 1: OD-H 5 tm 250 mmx20 mm / 2-Methylpentane; isopropyl alcohol / 25 °C / Resolution of racemate 2: hydrogen; palladium 10% on activated carbon / ethanol / 20 °C

  • 15
  • [ 100-72-1 ]
  • [ 51450-44-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C 1.2: 1.5 h / 0 - 20 °C 2.1: OD-H column / isopropyl alcohol; 2-Methylpentane / 25 °C / Resolution of racemate 3.1: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C 1.2: 1.5 h / 0 - 20 °C 2.1: Column: OD-H / 2-Methylpentane; isopropyl alcohol / 25 °C / Resolution of racemate 3.1: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C / 760.05 Torr
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C 1.2: 1.5 h / 0 - 20 °C 2.1: column: OD-H 5 μm 250 mm x 20 mm / 2-Methylpentane; isopropyl alcohol / 25 °C 3.1: palladium 10% on activated carbon; hydrogen / ethanol / 72 h / 20 °C
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C 1.2: 1.5 h / 0 - 20 °C 2.1: OD-H / isopropyl alcohol; 2-Methylpentane / 25 °C / Resolution of racemate 3.1: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C 1.2: 1.5 h / 0 - 20 °C 2.1: OD-H 5 tm 250 mmx20 mm / 2-Methylpentane; isopropyl alcohol / 25 °C / Resolution of racemate 3.1: hydrogen; palladium 10% on activated carbon / ethanol / 20 °C

  • 16
  • [ 51450-44-3 ]
  • tert-butyl 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-[(2S)-tetrahydro-2H-pyran-2-yl]propanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 1 h / -20 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.25 h / -78 °C / Inert atmosphere 2.2: 1.25 h / -78 - 20 °C
  • 17
  • [ 51450-44-3 ]
  • 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-[(2S)-tetrahydro-2H-pyran-2-yl]propanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 1 h / -20 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.25 h / -78 °C / Inert atmosphere 2.2: 1.25 h / -78 - 20 °C 3.1: trifluoroacetic acid / dichloromethane / 20 °C
  • 18
  • [ 51450-44-3 ]
  • (S)-6-(1-methyl-1H-pyrazol-4-yl)-4-(6-(4-((tetrahydro-2H-pyran-2-yl)methyl)piperazin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sulfur; potassium hydroxide / 20 °C 2: triethylamine / dichloromethane; N,N-dimethyl acetamide / 90 °C
  • 19
  • [ 51450-44-3 ]
  • [ 98-59-9 ]
  • (S)-(tetrahydro-2H-pyran-2-yl)methyl 4-methylbenzenesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% With sulfur; potassium hydroxide at 20℃; 684.1 Step 1: Preparation of (S)-(tetrahydro-2H-pyran-2-yl)methyl 4- methylbenzenesulfonate. A mixture of(S)-(tetrahydro-2H-pyran-2-yl)methanol (1 g, 8.61 mmol),sulfur (0.276 g, 8.61 mmol), TsC1 (1.81 g, 9.47 mmol), and KOH() (0.725 g, 12.9 mmol) in THF (10 mL) was stirred overnight at ambient temperature. The resulting suspension was filtered through a glass frit, rinsing with THF. The filtrate was concentrated in vacuo, and the resulting residue was purified by silica chromatography (100% DCM as eluent) to afford the title compound (1.33 g, 57% yield). ‘HNMR(CDC13) 7.79 (d, 2 H), 7.33 (d, 2 H), 3.95 (d, 2 H), 3.91-3.96 (m, 1 H), 3.50-3.56 (m, 1 H), 3.34-3.40 (m, 1 H), 2.44 (s, 3 H), 1.82-1.86 (m, 1 H), 1.41-1.59 (m, 4 H), 1.22-1.31 (m, 1 H).
  • 20
  • [ 51450-44-3 ]
  • tert-butyl 2-[5-chloro-4-(5-chloro-2-cyanophenyl)-2-oxopyridin-1(2H)-yl]-3-[(2S)-tetrahydro-2H-pyran-2-yl]propanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 1 h / -20 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.25 h / -78 °C / Inert atmosphere 2.2: 1.25 h / -78 - 20 °C
Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 1 h / -20 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.25 h / -78 °C / Inert atmosphere 2.2: 1.25 h / -78 - 20 °C
  • 21
  • [ 51450-44-3 ]
  • [ 358-23-6 ]
  • (2S)-tetrahydro-2H-pyran-2-ylmethyl trifluoromethanesulphonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In dichloromethane at -20℃; for 1h; 14.1.E General Method 7A: Preparation of Triflates General procedure: A solution of the appropriate alcohol (1 eq.) was initially charged in dichloromethane (0.1M), and at -20° C. lutidine (1.1-1.5 eq.) or triethylamine (1.1-1.5 eq.) and trifluoromethanesulphonic anhydride (1.05-1.5 eq.) were added in succession. The reaction mixture was stirred at -20° C. for another 1 h and then diluted with three times the amount (based on the reaction volume) of methyl tert-butyl ether. The organic phase was washed three times with a 3:1 mixture of saturated aqueous sodium chloride solution/1N hydrochloric acid and finally with saturated aqueous sodium hydrogencarbonate solution, dried (sodium sulphate or magnesium sulphate) and filtered, and the solvent was removed under reduced pressure. The crude product was used in the next stage without further purification.
With triethylamine In dichloromethane at -20℃; for 1h; 14.1E [0488] General Method 7A: Preparation of Triflates General procedure: [0489] A solution of the appropriate alcohol (1 eq.) was initially charged in dichloromethane (0. 1M), and at -20° C. lutidine (1.1-1.5 eq.) or triethylamine (1.1-1.5 eq.) and trifluoromethanesulphonic anhydride (1.05-1.5 eq.) were added in succession. The reaction mixture was stirred at-20° C. for another 1 h and then diluted with three times the amount (based on the reaction volume) of methyl tert-butyl ether. The organic phase was washed three times with a 3:1 mixture of saturated aqueous sodium chloride solutionllN hydrochloric acid and finally with saturated aqueous sodium hydrogencarbonate solution, dried (sodium sulphate or magnesium sulphate) and filtered, and the solvent was removed under reduced pressure. The crude product was used in the next stage without thrther purification.; [0712] According to General Method 7A, 330 mg (2.84 mmol) of (25)-tetrahydro-2H-pyran-2-ylmethanol were reacted with 0.57 ml (3.41 mmol, 1.2 eq.) of trifluoromethanesulphonic anhydride in the presence of 0.48 ml (3.41 mmol, 1.2 eq.) of triethylamine. The crude product was reacted in the next stage without further purification.10713] ‘H-NMR (400 MHz, DMSO-d5): ö [ppm]=4.32(dd, 1H), 4.18 (dd, 1H), 4.00-3.92 (m, 1H), 3.60-3.52 (m,1H), 3.48-3.39 (m, 1H), 1.85-1.74 (m, 1H), 1.56-1.41 (m,4H), 1.28-1.14 (m, 1H).
With 2,6-dimethylpyridine In dichloromethane at -78℃; for 0.5h; Inert atmosphere;
With triethylamine In dichloromethane at -20℃; for 1h; 2.1D General Method 7A: Preparation of Triflates A solution of the appropriate alcohol (1 eq.) was initially charged in dichloromethane (0.1 M), and at -20° C. lutidine (1.1-1.5 eq.) or triethylamine (1.1-1.5 eq.) and trifluoromethanesulphonic anhydride (1.05-1.5 eq.) were added in succession. The reaction mixture was stirred at-20° C. for another 1 hand then diluted with three times the amount (based on the reaction volume) of methyl tert-butyl ether. The organic phase was washed three times with a 3:1 mixture of saturated aqueous sodium chloride solutionllN hydrochloric acid and finally with saturated aqueous sodium hydrogencarbonate solution, dried (sodium sulphate or magnesium sulphate) and filtered, and the solvent was removed under reduced pressure. The crude product was used in the next stage without further purification.

  • 22
  • (tetra-2H-pyran-2-yl)methanol [ No CAS ]
  • [ 51450-44-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C 1.2: 1.5 h / 0 - 20 °C 2.1: OD-H 5 μm 250mmx20 mm / 2-Methylpentane; isopropyl alcohol / 25 °C / Resolution of racemate 3.1: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C / 760.05 Torr
  • 23
  • [ 1437318-78-9 ]
  • [ 51450-44-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: 1,1'-Thiocarbonyldiimidazole / 1,2-dichloro-ethane / 1.5 h / 23 - 60 °C / Inert atmosphere 1.2: 23 °C / Reflux; Inert atmosphere 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 14 h / 0 - 23 °C / Inert atmosphere
  • 24
  • (S)-triisopropyl((tetrahydro-2H-pyran-2-yl)methoxy)silane [ No CAS ]
  • [ 51450-44-3 ]
YieldReaction ConditionsOperation in experiment
1.39 g With tetrabutyl ammonium fluoride In tetrahydrofuran at 0 - 23℃; for 14h; Inert atmosphere;
  • 25
  • [ 51450-44-3 ]
  • (S)-2-(2-methylallyl)tetrahydro-2H-pyran [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 2: copper(I) bromide / tetrahydrofuran; acetonitrile / 14 h / -40 - 20 °C / Inert atmosphere
  • 26
  • [ 51450-44-3 ]
  • C9H18O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 2: copper(I) bromide / tetrahydrofuran; acetonitrile / 14 h / -40 - 20 °C / Inert atmosphere 3: hydrogen / methanol / 14 h / 760.05 Torr
  • 27
  • [ 51450-44-3 ]
  • (2S,6R)-2-isobutyl-6-((4-methoxybenzyl)oxy)tetrahydro-2H-pyran [ No CAS ]
  • (2S,6S)-2-isobutyl-6-((4-methoxybenzyl)oxy)tetrahydro-2H-pyran [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 2: copper(I) bromide / tetrahydrofuran; acetonitrile / 14 h / -40 - 20 °C / Inert atmosphere 3: hydrogen / methanol / 14 h / 760.05 Torr 4: C12H8ClF2I; sodium hydrogencarbonate; (R)-2,6-bis(4-cyclohexyl-2,6-diisopropylphenyl)-4-hydroxydinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepine 4-oxide / tert-butyl methyl ether / 24 h / 40 °C / Irradiation; Inert atmosphere; Molecular sieve; Sealed tube
  • 28
  • [ 51450-44-3 ]
  • (2R,3S)-4-(benzyloxy)-3-[(benzyloxy)carbonyl]amino}-4-oxobutan-2-yl 4-({2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-[(2S)-tetrahydro-2H-pyran-2-yl]propanoyl}amino)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: triethylamine / dichloromethane / 1 h / -20 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.25 h / -78 °C / Inert atmosphere 2.2: 1.25 h / -78 - 20 °C 3.1: trifluoroacetic acid / dichloromethane / 20 °C 4.1: N-ethyl-N,N-diisopropylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / N,N-dimethyl-formamide; ethyl acetate / 3 h / 80 °C 5.1: methanol; caesium carbonate / 4 h / 60 °C 6.1: dmap; dicyclohexyl-carbodiimide / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
  • 29
  • [ 51450-44-3 ]
  • ethyl 4-({2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-[(2S)-tetrahydro-2H-pyran-2-yl]propanoyl}amino)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: triethylamine / dichloromethane / 1 h / -20 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.25 h / -78 °C / Inert atmosphere 2.2: 1.25 h / -78 - 20 °C 3.1: trifluoroacetic acid / dichloromethane / 20 °C 4.1: N-ethyl-N,N-diisopropylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / N,N-dimethyl-formamide; ethyl acetate / 3 h / 80 °C
  • 30
  • [ 51450-44-3 ]
  • 4-({2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-[(2S)-tetrahydro-2H-pyran-2-yl]propanoyl}amino)benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: triethylamine / dichloromethane / 1 h / -20 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.25 h / -78 °C / Inert atmosphere 2.2: 1.25 h / -78 - 20 °C 3.1: trifluoroacetic acid / dichloromethane / 20 °C 4.1: N-ethyl-N,N-diisopropylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / N,N-dimethyl-formamide; ethyl acetate / 3 h / 80 °C 5.1: methanol; caesium carbonate / 4 h / 60 °C
  • 31
  • [ 51450-44-3 ]
  • O-[4-({2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-[(2S)-tetrahydro-2H-pyran-2-yl]propanoyl}amino)benzoyl]-L-threonine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: triethylamine / dichloromethane / 1 h / -20 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.25 h / -78 °C / Inert atmosphere 2.2: 1.25 h / -78 - 20 °C 3.1: trifluoroacetic acid / dichloromethane / 20 °C 4.1: N-ethyl-N,N-diisopropylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / N,N-dimethyl-formamide; ethyl acetate / 3 h / 80 °C 5.1: methanol; caesium carbonate / 4 h / 60 °C 6.1: dmap; dicyclohexyl-carbodiimide / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 7.1: hydrogen; palladium 10% on activated carbon / ethanol / 2.5 h / 20 °C
  • 32
  • [ 51450-44-3 ]
  • [ 75-36-5 ]
  • (S)-(tetrahydro-2H-pyran-2-yl)methyl acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With pyridine at 0 - 22℃; for 13h; Inert atmosphere; Sealed tube;
  • 33
  • [ 51450-44-3 ]
  • C18H21BrO4 [ No CAS ]
  • C18H21BrO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: carbon tetrabromide; triphenylphosphine / tetrahydrofuran / 17 h / 0 - 22 °C / Inert atmosphere; Sealed tube 2: [Cu((R)-Ph-BOX)(SbF6)2]; triphenylmethyl acetate / dichloromethane / 48 h / 60 °C / Inert atmosphere; Sealed tube
  • 34
  • [ 51450-44-3 ]
  • C18H21BrO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: carbon tetrabromide; triphenylphosphine / tetrahydrofuran / 17 h / 0 - 22 °C / Inert atmosphere; Sealed tube 2: C17H30CuN2O2(2+)*2F6Sb(1-); triphenylmethyl acetate / dichloromethane / 24 h / 60 °C / Inert atmosphere; Sealed tube
  • 35
  • [ 51450-44-3 ]
  • C20H24O6 [ No CAS ]
  • C20H24O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine / 13 h / 0 - 22 °C / Inert atmosphere; Sealed tube 2: [Cu((R)-Ph-BOX)(SbF6)2]; triphenylmethyl acetate / dichloromethane / 96 h / 60 °C / Inert atmosphere; Sealed tube
  • 36
  • [ 51450-44-3 ]
  • C20H24O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine / 13 h / 0 - 22 °C / Inert atmosphere; Sealed tube 2: C17H30CuN2O2(2+)*2F6Sb(1-); triphenylmethyl acetate / dichloromethane / 24 h / 60 °C / Inert atmosphere; Sealed tube
  • 37
  • [ 51450-44-3 ]
  • (S)-2-(bromomethyl)tetrahydro-2H-pyran [ No CAS ]
YieldReaction ConditionsOperation in experiment
26% With carbon tetrabromide; triphenylphosphine In tetrahydrofuran at 0 - 22℃; for 17h; Inert atmosphere; Sealed tube;
  • 38
  • [ 105499-32-9 ]
  • [ 51450-44-3 ]
YieldReaction ConditionsOperation in experiment
66% With dimethylsulfide borane complex In dichloromethane at 0 - 22℃; for 13h; Inert atmosphere; Sealed tube;
Same Skeleton Products
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