2-(4-Fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene CAS:898566-17-1 Empagliflozin / Dapagliflozin / Canagliflozin Intermediate HANGZHOU THINK CHEMICAL CO., LTD. (THINKCHEM) is an integrative corporation of trade, research and contract m
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inquiryProduct Description Product website: http://www.finerchem.com/pro01en/id/1695.html Product Name 2-(4-Fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene
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inquiry2-(4-Fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene Basic information Product Name: 2-(4-Fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene Synonyms: Thiophene, 2-(4-fluo
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inquiryChemical Name 2-(4-Fluorophenyl)-5-[(5-iodo-2-Methylphenyl)methyl]thiophene CAS Number 898566-17-1 Packing 25kg/drum Appearance: white
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inquiryAppearance:white or light yellow crystalline powder Storage:Store in a cool,dry place and keep away from direct strong light Package:As customer request Application:Used for research and industrial manufacture. Transportation:By Se
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inquiry(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)
Conditions | Yield |
---|---|
With triethylsilane; boron trifluoride diethyl etherate In dichloromethane; acetonitrile at 0 - 35℃; | 85% |
With sodium tetrahydroborate; chloro-trimethyl-silane; boron trifluoride diethyl etherate In dichloromethane; acetonitrile at 5 - 35℃; for 0.5h; | 81.1% |
With triethylsilane; boron trifluoride diethyl etherate In dichloromethane; acetonitrile at 0 - 28℃; Inert atmosphere; | 70.3% |
With aluminum (III) chloride; 1,1,3,3-Tetramethyldisiloxane In chlorobenzene at 10 - 50℃; Reagent/catalyst; Solvent; Concentration; Temperature; Industrial scale; | 65.2 kg |
With aluminum (III) chloride In chlorobenzene at 10 - 50℃; for 4h; | 11.48 g |
2-(4-fluorophenyl)thiophene
5-iodo-2-methylbenzoyl chloride
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)
Conditions | Yield |
---|---|
With aluminum (III) chloride Solvent; Temperature; Friedel-Crafts Acylation; | 80% |
Stage #1: 5-iodo-2-methylbenzoyl chloride With aluminum (III) chloride In dichloromethane at 2℃; for 0.25h; Stage #2: 2-(4-fluorophenyl)thiophene In dichloromethane at 2 - 20℃; for 2.41667h; Product distribution / selectivity; |
2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)
Conditions | Yield |
---|---|
With sodium iodide; N,N`-dimethylethylenediamine; copper(l) iodide In diethylene glycol dimethyl ether; toluene at 110℃; | |
With copper(l) iodide; sodium iodide; N,N`-dimethylethylenediamine In diethylene glycol dimethyl ether; toluene at 20℃; Inert atmosphere; Reflux; | |
With copper(l) iodide; sodium iodide; N,N`-dimethylethylenediamine In diethylene glycol dimethyl ether; toluene for 36h; Inert atmosphere; Reflux; | 94.9 g |
ortho-methylbenzoic acid
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: iodic acid / 20 °C / Molecular sieve 2: thionyl chloride 3: aluminum (III) chloride View Scheme |
5-iodo-2-methylbenzoic acid
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: thionyl chloride 2: aluminum (III) chloride View Scheme | |
Multi-step reaction with 3 steps 1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 20 °C / Inert atmosphere 2: aluminum (III) chloride / dichloromethane / 7.5 h / 0 - 20 °C / Inert atmosphere 3: triethylsilane; boron trifluoride diethyl etherate / dichloromethane; acetonitrile / 0 - 28 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide; thionyl chloride / chlorobenzene / 4 h / 65 - 70 °C / Inert atmosphere; Industrial scale 2: aluminum (III) chloride / chlorobenzene / 4 h / 50 - 55 °C / Industrial scale 3: aluminum (III) chloride; 1,1,3,3-Tetramethyldisiloxane / chlorobenzene / 10 - 50 °C / Industrial scale View Scheme | |
Multi-step reaction with 3 steps 1: thionyl chloride; N,N-dimethyl-formamide / chlorobenzene / 4 h / 65 - 70 °C / Inert atmosphere 2: aluminum (III) chloride / chlorobenzene / 4 h / 10 - 55 °C 3: aluminum (III) chloride / chlorobenzene / 4 h / 10 - 50 °C View Scheme |
5-iodo-2-methylbenzoyl chloride
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aluminum (III) chloride / dichloromethane / 7.5 h / 0 - 20 °C / Inert atmosphere 2: triethylsilane; boron trifluoride diethyl etherate / dichloromethane; acetonitrile / 0 - 28 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1: aluminum (III) chloride / chlorobenzene / 4 h / 50 - 55 °C / Industrial scale 2: aluminum (III) chloride; 1,1,3,3-Tetramethyldisiloxane / chlorobenzene / 10 - 50 °C / Industrial scale View Scheme |
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)
Conditions | Yield |
---|---|
With nickel(II) bromide dimethoxyethane; manganese; (4R,4'R)-4,4'-di(heptan-4-yl)-4,4',5,5'-tetrahydro-2,2'-bioxazole; tetra-(n-butyl)ammonium iodide In tetrahydrofuran at -10℃; for 22h; Sealed tube; Inert atmosphere; enantioselective reaction; | 95% |
methanol
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)
(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one
(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
Conditions | Yield |
---|---|
Stage #1: (2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene) With magnesium In tetrahydrofuran at 0 - 25℃; Inert atmosphere; Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran at 0℃; Inert atmosphere; Stage #3: methanol With methanesulfonic acid In tetrahydrofuran at 20℃; Inert atmosphere; | 93.3% |
Stage #1: (2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene) With s-butylmagnesium chloride; lithium chloride In tetrahydrofuran at -25 - -20℃; for 1h; Inert atmosphere; Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran at -25 - -20℃; for 2h; Stage #3: methanol With methanesulfonic acid for 18h; Reagent/catalyst; | 93.7% |
Stage #1: (2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene) With n-butyllithium In dibutyl ether; toluene Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In toluene Stage #3: methanol With methanesulfonic acid In toluene | |
Stage #1: (2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene) With TurboGrignard In tetrahydrofuran at -18 - -13℃; 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 at -15 - -10℃; for 1h; Large scale; Stage #3: methanol With hydrogenchloride at 20℃; for 1h; Large scale; | 23.5 kg |
tetraacetyl thioglucose
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)
Conditions | Yield |
---|---|
With palladium; triethylamine In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; | 90% |
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)
N,N-dimethyl-formamide
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; copper(II) nitrate trihydrate; water; acetic acid at 130℃; for 48h; | 87% |
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)
4-(p-methoxyphenyl)but-1-ene
Conditions | Yield |
---|---|
With dimethylsulfide borane complex; (6,6’-dimethyl-2,2'-bipyridine)nickel(II) dibromide; lithium methanolate In N,N-dimethyl acetamide at -19℃; for 12h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction; | 87% |
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)
2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide
(2S,3S,4R,5R,6R)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-6-(pivaloyloxymethyl)tetrahydro-2H-pyran-3,4,5-thiyl tris(2,2-dimethylpropanoate)
Conditions | Yield |
---|---|
Stage #1: (2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene) With n-butyllithium; zinc dibromide In n-heptane; dibutyl ether; toluene at -10 - 25℃; for 2.5h; Inert atmosphere; Stage #2: 2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide In n-heptane; dibutyl ether; toluene at 95℃; for 6.5h; Product distribution / selectivity; | 86.6% |
Stage #1: (2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene) With TurboGrignard In tetrahydrofuran at 0 - 10℃; for 1h; Large scale; Stage #2: 2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide In tetrahydrofuran at 0 - 10℃; for 3h; Large scale; | 85% |
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)
2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide
(3R,4R,5S)-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% |
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)
carbon dioxide
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 10h; Temperature; Solvent; Inert atmosphere; | 86.1% |
1-propenylbenzene
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)
Conditions | Yield |
---|---|
With potassium fluoride; dimethoxymethylsilane; (1,2-dimethoxyethane)dichloronickel(II); (4R,4'R)-1,1'-bis(3-(tert-butyl)phenyl)-4,4'-di(heptan-4-yl)-4,4',5,5'-tetrahydro-1H,1'H-2,2'-biimidazole at 22 - 26℃; for 24h; Sealed tube; enantioselective reaction; | 85% |
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)
(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one
Conditions | Yield |
---|---|
Stage #1: (2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene); (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one With n-butyllithium In tetrahydrofuran; hexane; toluene at -70℃; Industrial scale; Stage #2: With trifluoroacetic acid In tetrahydrofuran; hexane; water; toluene at 0℃; for 3h; Solvent; Reagent/catalyst; Temperature; Industrial scale; | 84.23% |
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)
Conditions | Yield |
---|---|
With n-hexyllithium; lithium bromide; zinc dibromide In hexane; dibutyl ether; toluene at 10 - 80℃; for 12h; | 79.1% |
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)
Conditions | Yield |
---|---|
With n-butyllithium; isopropylmagnesium chloride; lithium chloride In tetrahydrofuran; hexane at -10℃; for 3h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere; | 78.2% |
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)
bis(pinacol)diborane
Conditions | Yield |
---|---|
With 10H-phenothiazine; caesium carbonate In acetonitrile for 48h; Irradiation; Sealed tube; Inert atmosphere; | 78% |
methanesulfonic acid
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)
(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one
(2S,3R,4S,5S,6R)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-6-(hydroxylmethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
Conditions | Yield |
---|---|
Stage #1: (2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene); (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one With n-butyllithium In tetrahydrofuran; toluene at -85 - -65℃; for 2h; Stage #2: methanesulfonic acid In tetrahydrofuran; methanol; toluene at 20℃; for 16h; Time; | 77.5% |
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)
(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one
(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
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; toluene at -85 - -65℃; for 2h; Solvent; | 77.5% |
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; Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one at -60℃; for 1h; | |
Stage #1: (2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene) In tetrahydrofuran at 0 - 5℃; for 1h; Inert atmosphere; Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran at 0 - 5℃; for 2h; Stage #3: With methanesulfonic acid In methanol for 2h; Cooling; |
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)
Conditions | Yield |
---|---|
With n-hexyllithium; lithium bromide; zinc dibromide In hexane; dibutyl ether; toluene at 10 - 80℃; for 12h; | 76.1% |
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)
(4R,5S,6R)-4,5,6-tris(benzyloxy)-3-((benzyloxy)methyl)-2-cyclohexen-1-one
(1R,4R,5S,6R)-4,5,6-tris(benzyloxy)-3-(benzyloxymethyl)-1-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)cyclohex-2-enol
Conditions | Yield |
---|---|
Stage #1: (2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene) With TurboGrignard In tetrahydrofuran at -10℃; for 1h; Inert atmosphere; Stage #2: (4R,5S,6R)-4,5,6-tris(benzyloxy)-3-((benzyloxy)methyl)-2-cyclohexen-1-one In tetrahydrofuran at -10 - 0℃; for 4h; Inert atmosphere; | 75.6% |
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)
toluene-4-sulfonic acid
(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one
(2S,3R,4S,5S,6R)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-6-(hydroxylmethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
Conditions | Yield |
---|---|
Stage #1: (2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene); (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one With n-butyllithium In tetrahydrofuran; toluene at -85 - -65℃; for 2h; Stage #2: toluene-4-sulfonic acid In tetrahydrofuran; methanol; toluene at 20℃; for 16h; | 72.4% |
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)
2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide
Conditions | Yield |
---|---|
With lithium bromide; zinc dibromide In diethyl ether at -76℃; Temperature; Reagent/catalyst; Solvent; | 71% |
2,3,4,6-Tetra-O-benzyl-D-glucopyranose
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)
Conditions | Yield |
---|---|
Stage #1: 2,3,4,6-Tetra-O-benzyl-D-glucopyranose With sodium hydrogencarbonate; acetic acid; potassium bromide In dichloromethane; water at 20℃; for 0.25h; Stage #2: With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In water at 20 - 35℃; Stage #3: (2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene) With n-butyllithium In tetrahydrofuran; hexane at -70 - -30℃; Concentration; Solvent; Temperature; Inert atmosphere; | 70.2% |
(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
(3R,4R,5S)-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% |
allylbenzene
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)
bis(pinacol)diborane
Conditions | Yield |
---|---|
With [nickel(II)dichloride(dimethoxyethane)]; quinoline; lithium methanolate In 1,4-dioxane at 30℃; Inert atmosphere; Sealed tube; regioselective reaction; | 42% |
methanesulfonic acid
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)
2,3,4,6-tetra-O-acetyl-D-glucono-1,5-lactone
(2S,3R,4S,5S,6R)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-6-(hydroxylmethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
Conditions | Yield |
---|---|
Stage #1: (2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene) With TurboGrignard In tetrahydrofuran; toluene at -10 - -5℃; for 2h; Inert atmosphere; Stage #2: 2,3,4,6-tetra-O-acetyl-D-glucono-1,5-lactone In tetrahydrofuran; toluene at -45 - -40℃; for 2h; Inert atmosphere; Stage #3: methanesulfonic acid In methanol at 40℃; for 4h; | 37.5% |
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)
(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one
1-[1-hydroxy-2,3,4,6-tetra-O-(trimethylsilyl)-β-D-glucopyranosyl]-4-methyl-3-[[5-(4-fluorophenyl)-2-thienyl]methyl]benzene
Conditions | Yield |
---|---|
Stage #1: (2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene); (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one With trimethylsilylmethyllithium In tetrahydrofuran; hexane at -40℃; Stage #2: With water; sodium hydrogencarbonate In tetrahydrofuran; hexane at -40℃; |
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)
(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one
Conditions | Yield |
---|---|
Stage #1: (2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene) With TurboGrignard In tetrahydrofuran at 0 - 5℃; Inert atmosphere; Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran at 0 - 5℃; Product distribution / selectivity; Inert atmosphere; |
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)
2,3,4,6-tetra-O-acetyl-D-glucono-1,5-lactone
Conditions | Yield |
---|---|
Stage #1: (2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene) With sec-butylmagnesium chloride lithium chloride In toluene at -10 - 0℃; for 1.75h; Inert atmosphere; Stage #2: 2,3,4,6-tetra-O-acetyl-D-glucono-1,5-lactone In tetrahydrofuran; toluene at -35℃; for 1.25h; Inert atmosphere; Stage #3: With acetic acid In tetrahydrofuran; water; toluene at -35 - 25℃; Product distribution / selectivity; |
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)
canagliflozin
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: trimethylsilylmethyllithium / toluene; diethyl ether; pentane / 0.75 h / -50 °C / Inert atmosphere 1.2: 1 h / 25 °C 2.1: ethyl acetate; toluene / 21 h / 75 °C / Inert atmosphere 3.1: methanol / 16 h / 20 - 60 °C 4.1: water / 1 h / 0 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: n-hexyllithium / toluene; hexane; cyclopentyl methyl ether / 1.17 h / -45 - -25 °C / Inert atmosphere 2.1: zinc dibromide; lithium bromide / cyclopropyl methyl ether / -25 - 0 °C 2.2: 48.5 h / 20 - 65 °C 3.1: methanol / 16 h / 20 - 60 °C 4.1: water / 1 h / 0 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: acetic acid; potassium bromide; sodium hydrogencarbonate / water; dichloromethane / 0.25 h / 20 °C 1.2: 20 - 35 °C 1.3: -70 - -30 °C / Inert atmosphere 2.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 0.5 h / -40 - -20 °C / Inert atmosphere 3.1: trimethylsilyl iodide / dichloromethane / 0 - 30 °C View Scheme |
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