Dayangchem’s R&D center can offer custom synthesis according to the contract research and development services for the fine chemicals, pharmaceutical, biotechnique and some of the other chemicals. Near 20 years DayangChem has provided dif
Cas:761423-87-4
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inquiry(1S)-1,5-Anhydro-1-C-[3-[(1-benzothiophen-2-yl)methyl]-4-fluorophenyl]-D-glucitol Chemical Properties Boiling point 628.8±55.0 °C(Predicted) density 1.452 pka 13.27±0.70(Predicted) (1S)-1,5-Anhydro-1-C-[3-[(1-benzothiop
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inquiryHello, dear friend! I'm Hansen and Allen from China. Welcome to my lookchem mall! The following is a brief introduction of our company's products and services. If you are interested in our products, please contact us by emai
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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:As
Company Introduction 1. Established in 2005, with two independent business divisions: Fine chemicals division; Pharmaceutical division. 2. Main product: Optical brightener Textile auxiliary Dye stuff Pigments
Zibo Hangyu Biotechnology Development Co., Ltd is a leading manufacturer and supplier of chemicals in China. We develop produce and distribute high quality pharmaceuticals, intermediates, special chemicals and OLED intermediates and other fine chemi
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inquiryProduct name: Ipragliflozin CAS No.:761423-87-4 Molecule Formula:C21H21FO5S Molecule Weight:404.45 Purity: 99.0% Package: 25kg/drum Description:White powder Manufacture Standards:Enterprise Standard TESTING ITEMS
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inquiryDMF is available. Hangzhou Huarong Pharm Co., Ltd. established since 2009 , has been always focusing on supplying products and services to our clients in the field of small molecule drug. Huarong Pharm has built platforms for the research, deve
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inquiryLower price, sample is available,SDS test documents are available,large stock in warehouseAppearance:White powder Storage:Sealed and preserved Package:200/Kilograms Application:Fine chemical intermediates, used as the main raw material for the synthe
(1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-[3-[(1-benzothiophen-2-yl)methyl]-4-fluorophenyl]-D-sorbitol
A
(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
Conditions | Yield |
---|---|
With lithium hydroxide monohydrate; water In tetrahydrofuran; methanol at 15℃; for 4h; Temperature; Reagent/catalyst; Concentration; Industrial scale; | A 99.5% B 99% |
(1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-[3-[(1-benzothiophen-2-yl)methyl]-4-fluorophenyl]-D-sorbitol
(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
Conditions | Yield |
---|---|
Stage #1: (1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-[3-[(1-benzothiophen-2-yl)methyl]-4-fluorophenyl]-D-sorbitol With methanol; water; sodium hydroxide at 25 - 49.1℃; Stage #2: With hydrogenchloride In methanol; water at 20.2 - 60℃; | 97% |
With water; potassium carbonate In toluene at 10℃; | 80.1% |
(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
Conditions | Yield |
---|---|
With methanol; sodium methylate at 65℃; for 3h; | 95.3% |
(1S)-1,5-anhydro-1-[3-(1-benzothiophen-2-ylmethyl)-4-fluorophenyl]-2,3,4,6-tetra-O-benzyl - D-glucitol
(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
Conditions | Yield |
---|---|
Stage #1: (1S)-1,5-anhydro-1-[3-(1-benzothiophen-2-ylmethyl)-4-fluorophenyl]-2,3,4,6-tetra-O-benzyl - D-glucitol With boron trichloride In n-heptane; dichloromethane; pentamethylbenzene, at -78℃; for 3h; Inert atmosphere; Stage #2: With methanol In n-heptane; dichloromethane; pentamethylbenzene, at -78℃; | 87.8% |
With pentamethylbenzene,; boron trichloride In dichloromethane at -78℃; for 4h; Solvent; | 75% |
Stage #1: (1S)-1,5-anhydro-1-[3-(1-benzothiophen-2-ylmethyl)-4-fluorophenyl]-2,3,4,6-tetra-O-benzyl - D-glucitol With pentamethylbenzene,; boron trichloride In n-heptane; dichloromethane at -78℃; for 4h; Stage #2: With methanol In n-heptane; dichloromethane at -78 - 20℃; | 64% |
With pentamethylbenzene,; boron trichloride In n-heptane; dichloromethane at -78℃; for 2h; |
(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
Conditions | Yield |
---|---|
With triethylsilane; boron trichloride acetic acid In dichloromethane at -20 - 0℃; | 71.4% |
(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
Conditions | Yield |
---|---|
With triethylsilane; boron trichloride acetic acid In dichloromethane; acetonitrile at -20 - 0℃; | 70.2% |
(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
Conditions | Yield |
---|---|
Stage #1: 1-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-3,4,6-tri-O-tert-butyldimethylsilyl-D-glucal With borane-THF In tetrahydrofuran at 0℃; for 12h; Stage #2: With dihydrogen peroxide; sodium hydroxide at 20℃; for 24h; | 49% |
Stage #1: 1-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-3,4,6-tri-O-tert-butyldimethylsilyl-D-glucal With borane-THF In tetrahydrofuran at 0℃; for 12h; Stage #2: With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran; water at 20℃; for 24h; | 49% |
Multi-step reaction with 2 steps 1.1: borane-THF / tetrahydrofuran / 12 h / 0 °C 1.2: 24 h / 0 - 20 °C 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C View Scheme |
(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
Conditions | Yield |
---|---|
Stage #1: 1-(3-(benzo[b]thiophen-2-methyl)-4-fluorophenyl)-3-O-triisopropylsilyl-4,6-O-di-tert-butylsilylene-D-glucal With borane-THF In tetrahydrofuran at 0℃; for 12h; Stage #2: With dihydrogen peroxide; sodium hydroxide at 20℃; for 24h; | 45% |
Stage #1: 1-(3-(benzo[b]thiophen-2-methyl)-4-fluorophenyl)-3-O-triisopropylsilyl-4,6-O-di-tert-butylsilylene-D-glucal With borane-THF In tetrahydrofuran at 0℃; for 12h; Stage #2: With tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium hydroxide In water at 20℃; for 24h; | 45% |
(1-benzothiophen-2-yl)(5-bromo-2-fluorophenyl)methanol
(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 0.5 h / -20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane; toluene / 0.17 h / -78 °C 2.2: 2 h / -78 °C 3.1: pentamethylbenzene,; boron trichloride / n-heptane; dichloromethane / 4 h / -78 °C 3.2: -78 - 20 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 0.5 h / -20 °C 2.1: n-butyllithium / dibutyl ether; toluene; n-heptane / 2 h / -40 °C / Inert atmosphere 2.2: 2 h / 20 - 90 °C 3.1: pentamethylbenzene,; boron trichloride / dichloromethane / 4 h / -78 °C View Scheme |
2-[(5-bromo-2-fluorophenyl)methyl]-1-benzothiophene
(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane; toluene / 0.17 h / -78 °C 1.2: 2 h / -78 °C 2.1: pentamethylbenzene,; boron trichloride / n-heptane; dichloromethane / 4 h / -78 °C 2.2: -78 - 20 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: n-butyllithium / toluene; dibutyl ether / 3 h / -20 °C 1.2: 1 h / 0 °C 1.3: 3 h / 100 °C 2.1: sodium methylate; methanol / 3 h / 65 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: n-butyllithium / dibutyl ether; toluene; n-heptane / 2 h / -40 °C / Inert atmosphere 1.2: 2 h / 20 - 90 °C 2.1: pentamethylbenzene,; boron trichloride / dichloromethane / 4 h / -78 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 10 h / 80 °C / Schlenk technique 2.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine tetrafluoroborate; potassium hydroxide / tetrahydrofuran / 12 h / 80 °C / Sealed tube 3.1: borane-THF / tetrahydrofuran / 12 h / 0 °C 3.2: 24 h / 0 - 20 °C 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C View Scheme |
5-bromo-2-fluorobenzaldehyde
(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 1.2: 2 h / -78 °C 2.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 0.5 h / -20 °C 3.1: n-butyllithium / tetrahydrofuran; hexane; toluene / 0.17 h / -78 °C 3.2: 2 h / -78 °C 4.1: pentamethylbenzene,; boron trichloride / n-heptane; dichloromethane / 4 h / -78 °C 4.2: -78 - 20 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran / 1.5 h / -78 °C 1.2: 2 h / -78 °C 2.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 0.5 h / -20 °C 3.1: n-butyllithium / dibutyl ether; toluene; n-heptane / 2 h / -40 °C / Inert atmosphere 3.2: 2 h / 20 - 90 °C 4.1: pentamethylbenzene,; boron trichloride / dichloromethane / 4 h / -78 °C View Scheme |
Benzo[b]thiophene
(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 1.2: 2 h / -78 °C 2.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 0.5 h / -20 °C 3.1: n-butyllithium / tetrahydrofuran; hexane; toluene / 0.17 h / -78 °C 3.2: 2 h / -78 °C 4.1: pentamethylbenzene,; boron trichloride / n-heptane; dichloromethane / 4 h / -78 °C 4.2: -78 - 20 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran / 1.5 h / -78 °C 1.2: 2 h / -78 °C 2.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 0.5 h / -20 °C 3.1: n-butyllithium / dibutyl ether; toluene; n-heptane / 2 h / -40 °C / Inert atmosphere 3.2: 2 h / 20 - 90 °C 4.1: pentamethylbenzene,; boron trichloride / dichloromethane / 4 h / -78 °C View Scheme |
2,3,5,6-tetra-O-(tert-butyldimethylsilyl)-D-glucono-1,4-lactone
(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sec.-butyllithium / tetrahydrofuran; toluene; hexane / 2 h / -78 - -65 °C / Inert atmosphere 2: boron trichloride acetic acid; triethylsilane / dichloromethane / -20 - 0 °C View Scheme |
D-glucono-1,4-lactone
(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 4-methyl-morpholine / tetrahydrofuran / 1 h / -10 - 45 °C 2: n-butyllithium / tetrahydrofuran; toluene; hexane / 2 h / -78 - -65 °C / Inert atmosphere 3: boron trichloride acetic acid; triethylsilane / dichloromethane; acetonitrile / -20 - 0 °C View Scheme | |
Multi-step reaction with 3 steps 1: triethylamine / tetrahydrofuran / 1 h / -10 - 45 °C 2: sec.-butyllithium / tetrahydrofuran; toluene; hexane / 2 h / -78 - -65 °C / Inert atmosphere 3: boron trichloride acetic acid; triethylsilane / dichloromethane / -20 - 0 °C View Scheme |
(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran; toluene; hexane / 2 h / -78 - -65 °C / Inert atmosphere 2: boron trichloride acetic acid; triethylsilane / dichloromethane; acetonitrile / -20 - 0 °C View Scheme |
2-[(5-bromo-2-fluorophenyl)methyl]-1-benzothiophene
A
(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: s-butylmagnesium chloride; n-butyllithium; lithium chloride / tetrahydrofuran; hexane / 3.17 h / -10 °C / Inert atmosphere; Industrial scale 1.2: 3 h / -10 °C / Industrial scale 2.1: pyridine; dmap / dichloromethane / 2 h / 25 °C / Industrial scale 3.1: lithium hydroxide monohydrate; water / tetrahydrofuran; methanol / 4 h / 15 °C / Industrial scale View Scheme |
(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one
A
(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: s-butylmagnesium chloride; n-butyllithium; lithium chloride / tetrahydrofuran; hexane / 3.17 h / -10 °C / Inert atmosphere; Industrial scale 1.2: 3 h / -10 °C / Industrial scale 2.1: pyridine; dmap / dichloromethane / 2 h / 25 °C / Industrial scale 3.1: lithium hydroxide monohydrate; water / tetrahydrofuran; methanol / 4 h / 15 °C / Industrial scale View Scheme |
2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide
(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: n-butyllithium / toluene; dibutyl ether / 3 h / -20 °C 1.2: 1 h / 0 °C 1.3: 3 h / 100 °C 2.1: sodium methylate; methanol / 3 h / 65 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: n-butyllithium / toluene; hexane; dibutyl ether / 3.33 h / -20 °C / Inert atmosphere 1.2: 1.33 h / 0 °C / Inert atmosphere 1.3: 3 h / 100 °C / Inert atmosphere 2.1: sodium methylate; methanol / 3 h / 65 °C View Scheme |
(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: n-butyllithium / toluene; dibutyl ether / 3 h / -20 °C 1.2: 1 h / 0 °C 1.3: 3 h / 100 °C 2.1: sodium methylate; methanol / 3 h / 65 °C View Scheme |
(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: n-butyllithium / toluene; dibutyl ether / 3 h / -20 °C 1.2: 1 h / 0 °C 1.3: 3 h / 100 °C 2.1: sodium methylate; methanol / 3 h / 65 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: n-butyllithium / toluene; hexane; dibutyl ether / 3.33 h / -20 °C / Inert atmosphere 1.2: 1.33 h / 0 °C / Inert atmosphere 1.3: 3 h / 100 °C / Inert atmosphere 2.1: sodium methylate; methanol / 3 h / 65 °C View Scheme |
α-D-glucopyranose peracetylate
(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: hydrogen bromide; acetic acid / dichloromethane / 0.67 h / 0 °C 2.1: Acidic conditions 3.1: iron(II) sulfate / methanol / 12 h 4.1: n-butyllithium / dibutyl ether; toluene; n-heptane / 2 h / -40 °C / Inert atmosphere 4.2: 2 h / 20 - 90 °C 5.1: pentamethylbenzene,; boron trichloride / dichloromethane / 4 h / -78 °C View Scheme |
2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide
(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: Acidic conditions 2.1: iron(II) sulfate / methanol / 12 h 3.1: n-butyllithium / dibutyl ether; toluene; n-heptane / 2 h / -40 °C / Inert atmosphere 3.2: 2 h / 20 - 90 °C 4.1: pentamethylbenzene,; boron trichloride / dichloromethane / 4 h / -78 °C View Scheme |
1-bromo-α-D-glucopyranose
(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: iron(II) sulfate / methanol / 12 h 2.1: n-butyllithium / dibutyl ether; toluene; n-heptane / 2 h / -40 °C / Inert atmosphere 2.2: 2 h / 20 - 90 °C 3.1: pentamethylbenzene,; boron trichloride / dichloromethane / 4 h / -78 °C View Scheme |
2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl bromide
(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: n-butyllithium / dibutyl ether; toluene; n-heptane / 2 h / -40 °C / Inert atmosphere 1.2: 2 h / 20 - 90 °C 2.1: pentamethylbenzene,; boron trichloride / dichloromethane / 4 h / -78 °C View Scheme |
alpha-D-glucopyranose
(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: sodium acetate / 0.17 h / 140 °C 2.1: hydrogen bromide; acetic acid / dichloromethane / 0.67 h / 0 °C 3.1: Acidic conditions 4.1: iron(II) sulfate / methanol / 12 h 5.1: n-butyllithium / dibutyl ether; toluene; n-heptane / 2 h / -40 °C / Inert atmosphere 5.2: 2 h / 20 - 90 °C 6.1: pentamethylbenzene,; boron trichloride / dichloromethane / 4 h / -78 °C View Scheme |
(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine tetrafluoroborate; potassium hydroxide / tetrahydrofuran / 12 h / 80 °C / Sealed tube 2.1: borane-THF / tetrahydrofuran / 12 h / 0 °C 2.2: 24 h / 0 - 20 °C 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: tricyclohexylphosphine tetrafluoroborate; potassium hydroxide; bis(1,5-cyclooctadiene)nickel (0) / tetrahydrofuran / 12 h / 60 °C 2.1: borane-THF / tetrahydrofuran / 12 h / 0 °C 2.2: 24 h / 20 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C 1.2: 6 h / -35 °C / Inert atmosphere 2.1: 1H-imidazole / N,N-dimethyl-formamide / 6 h / -35 °C / Inert atmosphere 3.1: tricyclohexylphosphine tetrafluoroborate; potassium hydroxide; bis(1,5-cyclooctadiene)nickel (0) / tetrahydrofuran / 12 h / 60 °C 4.1: borane-THF / tetrahydrofuran / 12 h / 0 °C 4.2: 24 h / 20 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C 1.2: 6 h / -35 °C / Inert atmosphere 2.1: triisopropylsilyl chloride / N,N-dimethyl-formamide / 6 h / -35 °C / Inert atmosphere 3.1: tricyclohexylphosphine tetrafluoroborate; potassium hydroxide; bis(1,5-cyclooctadiene)nickel (0) / tetrahydrofuran / 60 - 80 °C 4.1: borane-THF / tetrahydrofuran / 12 h / 0 °C 4.2: 24 h / 20 °C View Scheme |
(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: tetrahydrofuran / -78 °C / Inert atmosphere 2.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine tetrafluoroborate; potassium hydroxide / tetrahydrofuran / 12 h / 80 °C / Sealed tube 3.1: borane-THF / tetrahydrofuran / 12 h / 0 °C 3.2: 24 h / 0 - 20 °C 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C View Scheme |
(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 - 20 °C 2.1: tetrahydrofuran / -78 °C / Inert atmosphere 3.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine tetrafluoroborate; potassium hydroxide / tetrahydrofuran / 12 h / 80 °C / Sealed tube 4.1: borane-THF / tetrahydrofuran / 12 h / 0 °C 4.2: 24 h / 0 - 20 °C 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 - 20 °C 1.2: -78 °C / Inert atmosphere 2.1: tricyclohexylphosphine tetrafluoroborate; potassium hydroxide; bis(1,5-cyclooctadiene)nickel (0) / tetrahydrofuran / 12 h / 60 °C 3.1: borane-THF / tetrahydrofuran / 12 h / 0 °C 3.2: 24 h / 20 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 - 20 °C 1.2: -78 °C / Inert atmosphere 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C 2.2: 6 h / -35 °C / Inert atmosphere 3.1: 1H-imidazole / N,N-dimethyl-formamide / 6 h / -35 °C / Inert atmosphere 4.1: tricyclohexylphosphine tetrafluoroborate; potassium hydroxide; bis(1,5-cyclooctadiene)nickel (0) / tetrahydrofuran / 12 h / 60 °C 5.1: borane-THF / tetrahydrofuran / 12 h / 0 °C 5.2: 24 h / 20 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 - 20 °C 1.2: -78 °C / Inert atmosphere 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C 2.2: 6 h / -35 °C / Inert atmosphere 3.1: triisopropylsilyl chloride / N,N-dimethyl-formamide / 6 h / -35 °C / Inert atmosphere 4.1: tricyclohexylphosphine tetrafluoroborate; potassium hydroxide; bis(1,5-cyclooctadiene)nickel (0) / tetrahydrofuran / 60 - 80 °C 5.1: borane-THF / tetrahydrofuran / 12 h / 0 °C 5.2: 24 h / 20 °C View Scheme |
(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine tetrafluoroborate; potassium hydroxide / tetrahydrofuran / 12 h / 80 °C / Sealed tube 2.1: borane-THF / tetrahydrofuran / 12 h / 0 °C 2.2: 24 h / 0 - 20 °C 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C View Scheme |
(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
L-proline
Ipragliflozin L-proline
Conditions | Yield |
---|---|
In dichloromethane at 35℃; for 3h; | 99% |
In ethanol; water at 100℃; for 0.5h; | 83.7% |
In ethanol at 100℃; for 0.5h; |
(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
p-toluenesulfonyl chloride
Conditions | Yield |
---|---|
With pyridine at 0℃; for 3h; | 72% |
(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
Conditions | Yield |
---|---|
Stage #1: (2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol With bis(tri-n-butyltin)oxide In chloroform for 2h; Inert atmosphere; Molecular sieve; Reflux; Stage #2: With bromine In dichloromethane; chloroform at 0℃; for 0.666667h; | 17% |
(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: pyridine / 3 h / 0 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 0 - 65 °C View Scheme |
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