The above product is Ality Chemical's strong item with best price, good quality and fast supply. Ality Chemical has been focusing on the research and production of this field for over 14 years. At the same time, we are always committed to providi
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inquiryName: Canagliflozin Tetraacetate Synonyms: (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate; (3(R),4(R),5(S)-triacetoxy-6(S)-{3-[5-(4-fluoro-phenyl)-thiophen-
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inquiryProduct Details Grade: pharmaceutical grade Purity:99%+ ProductionCapacity: 1000 Kilogram/Month Scope of use: For scientific research only(The product must be used legally) Our Advantage 1. Best quality with competitive price. 2. Quick shipping,
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inquiryProduct name: Canagliflozin Tetraacetate CAS No.: 866607-35-4 Molecule Formula:C32H33FO9S Molecule Weight:612.66 Purity: 99.0% Package: 25kg/drum Description:White crystalline powder Manufacture Standards:Enterprise Standard
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inquiryProduct Name: D-Glucitol, 1,5-anhydro-1-C-[3-[[5-(4-fluorophenyl)-2-thienyl]Methyl]-4-Methylphenyl]-, tetraacetate, (1S)- (9CI) Synonyms: D-Glucitol,1,5-anhydro-1-C-[3-[[5-(4-fluorophenyl)-2-thienyl]Methyl]-4-Methylphenyl]-, tetraacetate, (1S);
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inquiry(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)
2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide
(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
Conditions | Yield |
---|---|
Stage #1: (2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene) With isopropylmagnesium chloride In tetrahydrofuran at 0 - 10℃; for 2h; Inert atmosphere; Stage #2: 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide In tetrahydrofuran at -15 - 10℃; for 2h; Reagent/catalyst; Inert atmosphere; | 86.2% |
With bis(acetylacetonate)nickel(II); magnesium chloride; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine; zinc In tetrahydrofuran for 20h; Schlenk technique; Inert atmosphere; Cooling with ice; | 75% |
With magnesium chloride In tetrahydrofuran at 15℃; stereoselective reaction; | 60% |
(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In water; acetonitrile | 85% |
With triethylsilane; trifluoroborane diethyl ether In acetonitrile at 0 - 5℃; for 4h; | 22 g |
With triethylsilane; boron trifluoride diethyl etherate In acetonitrile at 0℃; for 4h; | 11.12 g |
With triethylsilane; boron trifluoride diethyl etherate In water; acetonitrile at 5 - 20℃; Temperature; Large scale; | 28.6 kg |
canagliflozin
acetic anhydride
(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
Conditions | Yield |
---|---|
With dmap; triethylamine In ethyl acetate at 20 - 30℃; for 1h; | 80% |
With 4-methyl-morpholine; dmap In tetrahydrofuran at -10 - 20℃; for 1.25h; | 78% |
With 4-methyl-morpholine; dmap In dichloromethane at -5 - 5℃; for 4h; Reagent/catalyst; | 69.5% |
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)
acetic anhydride
(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one
(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
Conditions | Yield |
---|---|
Stage #1: (2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene) With n-butyllithium In tetrahydrofuran; hexane at -75 - -70℃; for 1h; Inert atmosphere; Large scale; Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane at -60 - 20℃; for 1h; Large scale; Stage #3: acetic anhydride Large scale; Further stages; | 60% |
2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl chloride
(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
Conditions | Yield |
---|---|
With nickel(II) bromide dimethoxyethane; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; 4,4'-di-tert-butyl-2,2'-bipyridine; N,N,N',N'-tetramethylguanidine In acetonitrile at 25℃; for 24h; Inert atmosphere; Sealed tube; Irradiation; diastereoselective reaction; | 48% |
(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
Conditions | Yield |
---|---|
Stage #1: ((3R,4S,5R,6R)-6-(acetoxymethyl)-2-((5-(4-(fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triyl)triacetate With triethylsilane; boron trifluoride diethyl etherate In acetonitrile at 0 - 20℃; Stage #2: With water; potassium carbonate In acetonitrile at 20℃; Cooling with ice; |
(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
Conditions | Yield |
---|---|
Stage #1: (3(R),4(S),5(R)-triacetoxy-6-{3-[5-(4-fluoro-phenyl)-thiophen-2-ylmethyl]-4-methyl-phenyl}-6-hydroxy-tetrahydro-pyran-2(R)-yl)-methanol acetate With triethylsilane; boron trifluoride diethyl etherate In acetonitrile at 2℃; for 1.5h; Stage #2: With water; sodium carbonate In acetonitrile at 45℃; Product distribution / selectivity; |
2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran; toluene; hexane / -75 - -65 °C / Inert atmosphere 1.2: -75 - -70 °C 1.3: 12 h / -75 - 30 °C 2.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane / 0 - 5 °C 3.1: dmap / acetone / 5 h / 0.25 - 0.5 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: sodium iodide; copper(l) iodide; N,N`-dimethylethylenediamine / toluene; diethylene glycol dimethyl ether / 36 h / Inert atmosphere; Reflux 2.1: tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 2.2: 2 h / 0 - 5 °C 2.3: 2 h / Cooling 3.1: 4-methyl-morpholine; dmap / toluene; ethyl acetate / 15 h / 0 - 20 °C 4.1: triethylsilane; boron trifluoride diethyl etherate / acetonitrile / 4 h / 0 °C View Scheme |
4-fluoroboronic acid
(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,2-dimethoxyethane; water / 25 - 75 °C / Inert atmosphere 2.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.1 h / 25 - 30 °C / Inert atmosphere 2.2: 0 - 15 °C / Inert atmosphere 3.1: aluminum (III) chloride; sodium tetrahydroborate / 1,2-dimethoxyethane / 0 - 70 °C 4.1: n-butyllithium / tetrahydrofuran; toluene; hexane / -75 - -65 °C / Inert atmosphere 4.2: -75 - -70 °C 4.3: 12 h / -75 - 30 °C 5.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane / 0 - 5 °C 6.1: dmap / acetone / 5 h / 0.25 - 0.5 °C View Scheme |
2-(4-fluorophenyl)thiophene
(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.1 h / 25 - 30 °C / Inert atmosphere 1.2: 0 - 15 °C / Inert atmosphere 2.1: aluminum (III) chloride; sodium tetrahydroborate / 1,2-dimethoxyethane / 0 - 70 °C 3.1: n-butyllithium / tetrahydrofuran; toluene; hexane / -75 - -65 °C / Inert atmosphere 3.2: -75 - -70 °C 3.3: 12 h / -75 - 30 °C 4.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane / 0 - 5 °C 5.1: dmap / acetone / 5 h / 0.25 - 0.5 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: thionyl chloride / dichloromethane; N,N-dimethyl-formamide / 1 h / Reflux 1.2: 1 h / 0 - 30 °C 2.1: s-butylmagnesium chloride; lithium chloride / toluene; tetrahydrofuran / 2 h / -5 - 0 °C 2.2: -45 - -35 °C 3.1: boron trifluoride diethyl etherate; triethylsilane / acetonitrile / 1 h / 30 - 42 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: thionyl chloride / dichloromethane; N,N-dimethyl-formamide / 1 h / Reflux 1.2: 1 h / 0 - 30 °C 2.1: sodium tetrahydroborate / tetrahydrofuran; water / 4 h / 30 °C 3.1: methanesulfonic acid / methanol / 3 h / 30 °C 4.1: s-butylmagnesium chloride; lithium chloride / toluene; tetrahydrofuran / 2 h / -5 - 0 °C 4.2: -45 - -35 °C 5.1: boron trifluoride diethyl etherate; triethylsilane / acetonitrile / 1 h / 30 - 42 °C View Scheme |
(5-bromo-2-methylphenyl)[5-(p-fluorophenyl)thiophene-2-yl]methanone
(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: aluminum (III) chloride; sodium tetrahydroborate / 1,2-dimethoxyethane / 0 - 70 °C 2.1: n-butyllithium / tetrahydrofuran; toluene; hexane / -75 - -65 °C / Inert atmosphere 2.2: -75 - -70 °C 2.3: 12 h / -75 - 30 °C 3.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane / 0 - 5 °C 4.1: dmap / acetone / 5 h / 0.25 - 0.5 °C View Scheme |
5-iodo-2-methylbenzoic acid
(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: thionyl chloride / dichloromethane; N,N-dimethyl-formamide / 1 h / Reflux 1.2: 1 h / 0 - 30 °C 2.1: s-butylmagnesium chloride; lithium chloride / toluene; tetrahydrofuran / 2 h / -5 - 0 °C 2.2: -45 - -35 °C 3.1: boron trifluoride diethyl etherate; triethylsilane / acetonitrile / 1 h / 30 - 42 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: thionyl chloride / dichloromethane; N,N-dimethyl-formamide / 1 h / Reflux 1.2: 1 h / 0 - 30 °C 2.1: sodium tetrahydroborate / tetrahydrofuran; water / 4 h / 30 °C 3.1: methanesulfonic acid / methanol / 3 h / 30 °C 4.1: s-butylmagnesium chloride; lithium chloride / toluene; tetrahydrofuran / 2 h / -5 - 0 °C 4.2: -45 - -35 °C 5.1: boron trifluoride diethyl etherate; triethylsilane / acetonitrile / 1 h / 30 - 42 °C View Scheme |
(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: methanesulfonic acid / methanol / 3 h / 30 °C 2.1: s-butylmagnesium chloride; lithium chloride / toluene; tetrahydrofuran / 2 h / -5 - 0 °C 2.2: -45 - -35 °C 3.1: boron trifluoride diethyl etherate; triethylsilane / acetonitrile / 1 h / 30 - 42 °C View Scheme |
(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: s-butylmagnesium chloride; lithium chloride / toluene; tetrahydrofuran / 2 h / -5 - 0 °C 1.2: -45 - -35 °C 2.1: boron trifluoride diethyl etherate; triethylsilane / acetonitrile / 1 h / 30 - 42 °C View Scheme |
2,3,4,6-tetra-O-acetyl-D-glucono-1,5-lactone
(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: s-butylmagnesium chloride; lithium chloride / toluene; tetrahydrofuran / 2 h / -5 - 0 °C 1.2: -45 - -35 °C 2.1: boron trifluoride diethyl etherate; triethylsilane / acetonitrile / 1 h / 30 - 42 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: s-butylmagnesium chloride; lithium chloride / toluene; tetrahydrofuran / 2 h / -5 - 0 °C 1.2: -45 - -35 °C 2.1: boron trifluoride diethyl etherate; triethylsilane / acetonitrile / 1 h / 30 - 42 °C View Scheme |
(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
Conditions | Yield |
---|---|
With triethylsilane; boron trifluoride diethyl etherate In acetonitrile at 30 - 42℃; for 1h; | 73 g |
D-Glucono-1,5-lactone
(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: trifluoroacetic acid 2.1: s-butylmagnesium chloride; lithium chloride / toluene; tetrahydrofuran / 2 h / -5 - 0 °C 2.2: -45 - -35 °C 3.1: boron trifluoride diethyl etherate; triethylsilane / acetonitrile / 1 h / 30 - 42 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: trifluoroacetic acid 2.1: s-butylmagnesium chloride; lithium chloride / toluene; tetrahydrofuran / 2 h / -5 - 0 °C 2.2: -45 - -35 °C 3.1: boron trifluoride diethyl etherate; triethylsilane / acetonitrile / 1 h / 30 - 42 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: tetrahydrofuran; 1-methyl-pyrrolidin-2-one / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -75 - -70 °C / Inert atmosphere 2.2: 1 h / -60 °C 3.1: dmap; methylamine / 1-methyl-pyrrolidin-2-one / 1 h / 0 - 30 °C 4.1: triethylsilane; trifluoroborane diethyl ether / acetonitrile / 4 h / 0 - 5 °C View Scheme | |
Multi-step reaction with 4 steps 1: 4-methyl-morpholine / tetrahydrofuran 2: n-butyllithium / toluene; dibutyl ether 3: dmap; 4-methyl-morpholine / dichloromethane 4: boron trifluoride diethyl etherate / acetonitrile; water View Scheme | |
Multi-step reaction with 2 steps 1.1: 4-methyl-morpholine / tetrahydrofuran / 20 °C / Inert atmosphere; Large scale 2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -75 - -70 °C / Inert atmosphere; Large scale 2.2: 1 h / -60 - 20 °C / Large scale 2.3: Large scale View Scheme |
(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: s-butylmagnesium chloride; lithium chloride / toluene; tetrahydrofuran / 2 h / -5 - 0 °C 1.2: -45 - -35 °C 2.1: boron trifluoride diethyl etherate; triethylsilane / acetonitrile / 1 h / 30 - 42 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: sodium tetrahydroborate / tetrahydrofuran; water / 4 h / 30 °C 2.1: methanesulfonic acid / methanol / 3 h / 30 °C 3.1: s-butylmagnesium chloride; lithium chloride / toluene; tetrahydrofuran / 2 h / -5 - 0 °C 3.2: -45 - -35 °C 4.1: boron trifluoride diethyl etherate; triethylsilane / acetonitrile / 1 h / 30 - 42 °C View Scheme |
(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
Conditions | Yield |
---|---|
With triethylsilane; boron trifluoride diethyl etherate In acetonitrile at 30 - 42℃; for 1h; | 73 g |
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)
(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 1.2: 2 h / 0 - 5 °C 1.3: 2 h / Cooling 2.1: 4-methyl-morpholine; dmap / toluene; ethyl acetate / 15 h / 0 - 20 °C 3.1: triethylsilane; boron trifluoride diethyl etherate / acetonitrile / 4 h / 0 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: TurboGrignard / tetrahydrofuran / 1 h / -18 - -13 °C / Inert atmosphere; Large scale 1.2: 1 h / -15 - -10 °C / Large scale 1.3: 1 h / 20 °C / Large scale 2.1: dmap; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0 - 10 °C / Large scale 3.1: triethylsilane; boron trifluoride diethyl etherate / acetonitrile; water / 5 - 20 °C / Large scale View Scheme |
(3R,4S,5S,6R)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: dmap; methylamine / 1-methyl-pyrrolidin-2-one / 1 h / 0 - 30 °C 2: triethylsilane; trifluoroborane diethyl ether / acetonitrile / 4 h / 0 - 5 °C View Scheme | |
Multi-step reaction with 2 steps 1: 4-methyl-morpholine; dmap / toluene; ethyl acetate / 15 h / 0 - 20 °C 2: triethylsilane; boron trifluoride diethyl etherate / acetonitrile / 4 h / 0 °C View Scheme | |
Multi-step reaction with 2 steps 1: dmap; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0 - 10 °C / Large scale 2: triethylsilane; boron trifluoride diethyl etherate / acetonitrile; water / 5 - 20 °C / Large scale View Scheme |
(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one
(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -75 - -70 °C / Inert atmosphere 1.2: 1 h / -60 °C 2.1: dmap; methylamine / 1-methyl-pyrrolidin-2-one / 1 h / 0 - 30 °C 3.1: triethylsilane; trifluoroborane diethyl ether / acetonitrile / 4 h / 0 - 5 °C View Scheme | |
Multi-step reaction with 3 steps 1: n-butyllithium / toluene; dibutyl ether 2: dmap; 4-methyl-morpholine / dichloromethane 3: boron trifluoride diethyl etherate / acetonitrile; water View Scheme | |
Multi-step reaction with 3 steps 1.1: TurboGrignard / tetrahydrofuran / 1 h / -18 - -13 °C / Inert atmosphere; Large scale 1.2: 1 h / -15 - -10 °C / Large scale 1.3: 1 h / 20 °C / Large scale 2.1: dmap; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0 - 10 °C / Large scale 3.1: triethylsilane; boron trifluoride diethyl etherate / acetonitrile; water / 5 - 20 °C / Large scale View Scheme |
2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide
A
(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
Conditions | Yield |
---|---|
With dichloro(1,2-{bis[3,5-bis(trimethylsilyl)pheny]phosphino-κP}benzene)iron(II) In tetrahydrofuran at 0 - 25℃; for 36h; Inert atmosphere; Overall yield = 0.467 g; diastereoselective reaction; | A 0.168 g B 0.236 g |
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)
2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide
A
(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
Conditions | Yield |
---|---|
With nickel(II) perchlorate hexahydrate; 4,4'-di-tert-butyl-2,2'-bipyridine; magnesium chloride; zinc In N,N-dimethyl acetamide Reagent/catalyst; Solvent; Temperature; Schlenk technique; Inert atmosphere; Cooling with ice; Overall yield = 80 %; Optical yield = 20 %de; | |
With dmap; nickel(II) perchlorate hexahydrate; hydrogen bromide; acetic acid; magnesium chloride; zinc In tetrahydrofuran at 25℃; for 12h; Schlenk technique; Sealed tube; Inert atmosphere; Overall yield = 57.5 mg; stereoselective reaction; | A n/a B n/a |
α-D-glucopyranose peracetylate
(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: hydrogen bromide; acetic acid / dichloromethane / 2 h / 0 - 10 °C 2.1: isopropylmagnesium chloride / tetrahydrofuran / 2 h / 0 - 10 °C / Inert atmosphere 2.2: 2 h / -15 - 10 °C / Inert atmosphere View Scheme |
β-D-glucose pentaacetate
(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: titanium tetrachloride / chloroform / 3 h / 70 °C 2: [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; nickel(II) bromide dimethoxyethane; N,N,N',N'-tetramethylguanidine; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; 4,4'-di-tert-butyl-2,2'-bipyridine / acetonitrile / 24 h / 25 °C / Inert atmosphere; Sealed tube; Irradiation View Scheme |
(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
canagliflozin
Conditions | Yield |
---|---|
With methanol; sodium methylate at 20℃; for 12h; Sealed tube; | 99% |
With water; sodium hydroxide In tetrahydrofuran; methanol at 20 - 25℃; for 1.16667h; | 98% |
With di(n-butyl)tin oxide In methanol for 24h; Reflux; Inert atmosphere; | 95% |
(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
Conditions | Yield |
---|---|
With methanol; lithium hydroxide In tetrahydrofuran; water at 0 - 20℃; for 2h; |
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