Methyl 1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-alpha-D-glucopyranoside CAS No.:714269-57-5 HANGZHOU THINK CHEMICAL CO., LTD. (THINKCHEM) is an integrative corporation of trade, research and contract manufacture. With about ten years
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inquiryThe 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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inquiryProduct Description Product website: http://www.finerchem.com/pro01en/id/1693.html Product Name Methyl 1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-alpha-D-glucopyranoside
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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
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A substitute for perfluorooctanoic acid, mainly used as a surfactant, dispersant, additive, etc Appearance:White solid or Colorless liquid Purity:99.3 % We will ship the goods in a timely manner as required We can provide relevant documents acc
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inquiryBoiling Point:609.6±55.0 °C(Predicted) PKA:12.59±0.70(Predicted) PSA:108.61000 Density:1.39±0.1 g/cm3 (20 oC 760 Torr) LogP:1.60250 Storage Temp.:2-8°C Solubility.:Acetonitrile (Slightly), DMSO (Slightly), M
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inquiryMethyl 1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-alpha-D-glucopyranosideAppearance:White powder Storage:cool and seal Package:according to customers' requirements Application:Dapagliflozin intermediate Transportation:By air(EMS or EUB or FedEx
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inquiryWe are one of a few suppliers that can offer custom synthesis service of this product We are specialized in custom synthesis, chemical/pharmaceutical/ pesticides outsourcing and contract research. We are committed to prov
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inquiryProduct name: Methyl 1-C-[4-Chloro-3-(4-Ethoxybenzyl)Phenyl]-Alpha-D-Glucopyranoside CAS No.:714269-57-5 Molecule Formula:C22H27ClO7 Molecule Weight:438.89 Purity: 99% Package: 25kg/drum Description:White powder Manufacture Standards:Enterpris
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inquiryHuarong Industrial Group Limited established since 2006 , has been actively developing specialty products for Finished Dosages, APIs, Intermediates, and Fine chemicals markets in North America, Europe, Korea, Japan, Mid-East and all over the World.
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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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inquiryfactory?direct?saleAppearance:White Powder Storage:Store In Dry, Cool And Ventilated Place Package:25kg/drum, also according to the clients requirement Application:It is widely used as a thickener, emulsifier and stabilizer Transportation:By Sea Or B
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inquiry1-chloro-2-(4-ethoxybenzyl)-4-iodobenzene
(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-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
Conditions | Yield |
---|---|
Stage #1: 1-chloro-2-(4-ethoxybenzyl)-4-iodobenzene; (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one With TurboGrignard In tetrahydrofuran at -30 - -20℃; for 1h; Inert atmosphere; Stage #2: With methanesulfonic acid In tetrahydrofuran; methanol at -10 - 30℃; for 2h; Inert atmosphere; | 81.8% |
methanesulfonic acid
(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
Conditions | Yield |
---|---|
In methanol at 20℃; for 10h; | 81.4% |
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; hexane; toluene at -78 - -65℃; for 2h; Inert atmosphere; | 78.6% |
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
(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-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
Conditions | Yield |
---|---|
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With sec.-butyllithium In tetrahydrofuran; cyclohexane at -78 - -68℃; for 1h; Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; n-heptane; cyclohexane at -78 - -68℃; for 30h; | 78.3% |
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran; hexane; toluene at -78℃; for 1h; Large scale; Stage #2: (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 -78℃; for 3h; Large scale; | 78% |
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran; hexane; toluene at -78℃; for 1h; Inert atmosphere; Industrial scale; Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one With methanesulfonic acid In tetrahydrofuran; methanol; hexane; toluene at -78 - 40℃; for 14h; Industrial scale; | 78% |
Multi-step reaction with 2 steps 1.1: N,N,N',N'',N'''-pentamethyldiethylenetriamine; n-butyllithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 1.2: 2 h / -78 °C / Inert atmosphere 2.1: methanol / 10 h / 20 °C View Scheme |
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
methanesulfonic 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-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
Conditions | Yield |
---|---|
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran; hexane; toluene at -78℃; 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; toluene at -78℃; for 3h; Large scale; Stage #3: methanesulfonic acid In methanol at 0 - 40℃; for 11h; Large scale; | 78% |
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
2,3,5,6-tetra-O-(tert-butyldimethylsilyl)-D-glucono-1,4-lactone
(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; hexane; toluene at -78 - -65℃; for 2h; Inert atmosphere; | 77.3% |
methanol
(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid at 20℃; for 12h; Inert atmosphere; | 71.6% |
With n-butyllithium; toluene-4-sulfonic acid at 20℃; for 12h; | 141.5 g |
(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In methanol at 20 - 30℃; for 12h; Inert atmosphere; | 71.6% |
methanol
(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
Conditions | Yield |
---|---|
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran; hexane; toluene at -30℃; Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane; toluene at -30 - -24℃; Stage #3: methanol In tetrahydrofuran; hexane; toluene at -10 - 35℃; for 23h; Acidic conditions; |
(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-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.67 h / -78 °C / Inert atmosphere 1.2: 5 h / -78 °C / Inert atmosphere 2.1: toluene-4-sulfonic acid / 12 h / 20 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.67 h / -78 °C 1.2: 5 h / -78 °C 2.1: n-butyllithium; toluene-4-sulfonic acid / 12 h / 20 °C View Scheme |
methanol
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
(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-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
Conditions | Yield |
---|---|
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran; hexane; toluene at -65℃; Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane; toluene at -65℃; for 2h; Stage #3: methanol With hydrogenchloride; water In tetrahydrofuran; hexane; toluene at 20℃; | |
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene; (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one With n-butyllithium In tetrahydrofuran at -85 - -70℃; for 2h; Inert atmosphere; Stage #2: methanol With methanesulfonic acid In tetrahydrofuran at -75 - 15℃; for 18h; Inert atmosphere; | |
With n-butyllithium; methanesulfonic acid In tetrahydrofuran; toluene at -15 - 5℃; for 0.0113889h; |
2-chloro-5-iodobenzoylchloride
(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: aluminum (III) chloride / dichloromethane / 0.5 h / -3 - 5 °C 1.2: 12 h / 0 - 25 °C 1.3: polymethylhydrosiloxane (PMHS) / 16 h / 30 °C 2.1: TurboGrignard / tetrahydrofuran / 1.5 h / -5 - 0 °C / Inert atmosphere 2.2: 1 h / -5 - 0 °C 2.3: 16 h / -10 - 20 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: aluminum (III) chloride / dichloromethane / 2 h / 0 - 5 °C 1.2: polymethylhydrosiloxane / 26 h / 25 - 30 °C 2.1: TurboGrignard / tetrahydrofuran / 0.67 h / -60 - -50 °C / Inert atmosphere 2.2: 5.67 h / -60 - -50 °C / Inert atmosphere 2.3: 18 h / -10 - 15 °C View Scheme |
Phenetole
(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 15 h / 25 - 30 °C 1.2: 2 h / 0 - 10 °C 2.1: aluminum (III) chloride; sodium tetrahydroborate / Dimethyl ether / 30 h / 0 - 65 °C 3.1: n-butyllithium / tetrahydrofuran; toluene / 1 h / -75 - -60 °C 3.2: 3 h / -75 - -60 °C 3.3: 18 h / -75 - 25 °C View Scheme |
D-Glucono-1,5-lactone
(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: 4-methyl-morpholine / tetrahydrofuran / 17 h / 5 - 25 °C / Inert atmosphere; Large scale 2.1: TurboGrignard / tetrahydrofuran / 0.67 h / -60 - -50 °C / Inert atmosphere 2.2: 5.67 h / -60 - -50 °C / Inert atmosphere 2.3: 18 h / -10 - 15 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: 4-methyl-morpholine / tetrahydrofuran / 10 h / 20 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; hexane / 0.67 h / -78 °C / Inert atmosphere 2.2: 5 h / -78 °C / Inert atmosphere 3.1: toluene-4-sulfonic acid / 12 h / 20 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1.1: 4-methyl-morpholine / tetrahydrofuran / 8 h / 20 - 30 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; hexane / 0.67 h / -78 °C / Inert atmosphere 2.2: 5 h / -78 °C / Inert atmosphere 3.1: toluene-4-sulfonic acid / methanol / 12 h / 20 - 30 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1.1: 4-methyl-morpholine / tetrahydrofuran / 10 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 0.67 h / -78 °C 2.2: 5 h / -78 °C 3.1: n-butyllithium; toluene-4-sulfonic acid / 12 h / 20 °C View Scheme |
2-chloro-5-iodobenzoic acid
(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 16.17 h / 10 - 25 °C 2.1: aluminum (III) chloride / dichloromethane / 0.5 h / -3 - 5 °C 2.2: 12 h / 0 - 25 °C 2.3: polymethylhydrosiloxane (PMHS) / 16 h / 30 °C 3.1: TurboGrignard / tetrahydrofuran / 1.5 h / -5 - 0 °C / Inert atmosphere 3.2: 1 h / -5 - 0 °C 3.3: 16 h / -10 - 20 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 16 h / 10 - 25 °C 2.1: aluminum (III) chloride / dichloromethane / 2 h / 0 - 5 °C 2.2: polymethylhydrosiloxane / 26 h / 25 - 30 °C 3.1: TurboGrignard / tetrahydrofuran / 0.67 h / -60 - -50 °C / Inert atmosphere 3.2: 5.67 h / -60 - -50 °C / Inert atmosphere 3.3: 18 h / -10 - 15 °C View Scheme |
methanol
(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol
(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
Conditions | Yield |
---|---|
With hydrogenchloride In tetrahydrofuran at -10 - 15℃; for 18h; Temperature; | |
With methanesulfonic acid In neat (no solvent) at 20℃; for 6h; Inert atmosphere; |
methanol
1-chloro-2-(4-ethoxybenzyl)-4-iodobenzene
(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-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
Conditions | Yield |
---|---|
Stage #1: 1-chloro-2-(4-ethoxybenzyl)-4-iodobenzene With TurboGrignard In tetrahydrofuran at -5 - 0℃; for 1.5h; Inert atmosphere; Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one With TurboGrignard In tetrahydrofuran; n-heptane at -5 - 0℃; for 1h; Stage #3: methanol With hydrogenchloride In tetrahydrofuran; n-heptane; water at -10 - 20℃; for 16h; Concentration; Temperature; | |
Stage #1: 1-chloro-2-(4-ethoxybenzyl)-4-iodobenzene With TurboGrignard In tetrahydrofuran at -60 - -50℃; for 0.666667h; 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; n-heptane at -60 - -50℃; for 5.66667h; Inert atmosphere; Stage #3: methanol With hydrogenchloride; water In tetrahydrofuran at -10 - 15℃; for 18h; Temperature; Time; |
C34H59ClO7Si4
(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
Conditions | Yield |
---|---|
With water; sodium hydroxide In tetrahydrofuran; hexane; toluene for 1h; | 7.69 kg |
(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.67 h / -78 °C / Inert atmosphere 1.2: 5 h / -78 °C / Inert atmosphere 2.1: toluene-4-sulfonic acid / methanol / 12 h / 20 - 30 °C / Inert atmosphere View Scheme |
D-glucono-1,4-lactone
(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 4-methyl-morpholine / tetrahydrofuran / 1 h / -10 - 45 °C 2: n-butyllithium / tetrahydrofuran; toluene; hexane / 2 h / -78 - -65 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1: triethylamine / tetrahydrofuran / 1 h / -10 - 45 °C 2: n-butyllithium / tetrahydrofuran; toluene; hexane / 2 h / -78 - -65 °C / Inert atmosphere View Scheme |
1-chloro-2-(4-ethoxybenzyl)-4-iodobenzene
(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one
A
(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
Conditions | Yield |
---|---|
Stage #1: 1-chloro-2-(4-ethoxybenzyl)-4-iodobenzene With TurboGrignard In tetrahydrofuran at -5 - 0℃; 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 5℃; for 3h; Inert atmosphere; Stage #3: With hydrogenchloride; methanol In tetrahydrofuran Inert atmosphere; |
5-bromo-2-chlorobenzoic acid
(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 15 h / 25 - 30 °C 1.2: 2 h / 0 - 10 °C 2.1: aluminum (III) chloride; sodium tetrahydroborate / Dimethyl ether / 30 h / 0 - 65 °C 3.1: n-butyllithium / tetrahydrofuran; toluene / 1 h / -75 - -60 °C 3.2: 3 h / -75 - -60 °C 3.3: 18 h / -75 - 25 °C View Scheme |
(5-bromo-2-chlorophenyl)(4-ethyloxyphenyl)methanone
(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: aluminum (III) chloride; sodium tetrahydroborate / Dimethyl ether / 30 h / 0 - 65 °C 2.1: n-butyllithium / tetrahydrofuran; toluene / 1 h / -75 - -60 °C 2.2: 3 h / -75 - -60 °C 2.3: 18 h / -75 - 25 °C View Scheme |
(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: 4-methyl-morpholine / tetrahydrofuran / 15 h / 0 - 40 °C 2.1: n-butyllithium / tetrahydrofuran; toluene / 1 h / -75 - -60 °C 2.2: 3 h / -75 - -60 °C 2.3: 18 h / -75 - 25 °C View Scheme |
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
Conditions | Yield |
---|---|
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran; toluene at -75 - -60℃; for 1h; Stage #2: 3,4,5-tris[(trimethylsilyl)oxy]-6-{[(trimethylsilyl)oxy]methyl}-tetrahydro-2H-pyran-2-one In tetrahydrofuran; toluene at -75 - -60℃; for 3h; Stage #3: With methanesulfonic acid In tetrahydrofuran; methanol; toluene at -75 - 25℃; for 18h; | 82 g |
2-chloro-benzaldehyde
(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: N-Bromosuccinimide / dichloromethane / 10.5 h / 5 °C / Large scale 2.1: sodium tetrahydroborate / ethanol / 4 h / 20 °C / Large scale 3.1: thionyl chloride / 3 h / 70 °C / Large scale 4.1: aluminum (III) chloride / ethyl acetate / 9 h / 78 °C / Cooling with ice; Large scale 5.1: n-butyllithium / tetrahydrofuran; toluene; hexane / 1 h / -78 °C / Large scale 5.2: 3 h / -78 °C / Large scale View Scheme |
2-chloro-5-bromobenzaldehyde
(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: sodium tetrahydroborate / ethanol / 4 h / 20 °C / Large scale 2.1: thionyl chloride / 3 h / 70 °C / Large scale 3.1: aluminum (III) chloride / ethyl acetate / 9 h / 78 °C / Cooling with ice; Large scale 4.1: n-butyllithium / tetrahydrofuran; toluene; hexane / 1 h / -78 °C / Large scale 4.2: 3 h / -78 °C / Large scale View Scheme |
5-bromo-2-chlorobenzyl alcohol
(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: thionyl chloride / 3 h / 70 °C / Large scale 2.1: aluminum (III) chloride / ethyl acetate / 9 h / 78 °C / Cooling with ice; Large scale 3.1: n-butyllithium / tetrahydrofuran; toluene; hexane / 1 h / -78 °C / Large scale 3.2: 3 h / -78 °C / Large scale View Scheme |
(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: aluminum (III) chloride / ethyl acetate / 9 h / 78 °C / Cooling with ice; Large scale 2.1: n-butyllithium / tetrahydrofuran; toluene; hexane / 1 h / -78 °C / Large scale 2.2: 3 h / -78 °C / Large scale View Scheme |
4-bromo-aniline
(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: water; methanol / 5 h / 20 °C / Cooling with ice; Large scale 2.1: aluminum (III) chloride / ethyl acetate / 8 h / Cooling with ice; Reflux; Large scale 3.1: hydrogenchloride / water; methanol / 6 h / 80 °C / Large scale 4.1: hydrogenchloride; sodium nitrite / water / 3 h / -5 - 0 °C / Large scale 4.2: 4 h / 20 - 80 °C / Large scale 5.1: n-butyllithium / tetrahydrofuran; toluene; hexane / 1 h / -78 °C / Inert atmosphere; Large scale 5.2: 3 h / -78 °C / Large scale 5.3: 11 h / 0 - 40 °C / Large scale View Scheme | |
Multi-step reaction with 5 steps 1.1: water; methanol / 5.5 h / 20 °C / Cooling with ice; Industrial scale 2.1: hydrogen fluoride / ethyl acetate / 8.5 h / Cooling with ice; Industrial scale 3.1: hydrogenchloride / water; methanol / 6 h / 80 °C / Industrial scale 4.1: hydrogenchloride; sodium nitrite / water / 3 h / -5 °C / Industrial scale 4.2: 4 h / 20 - 80 °C / Industrial scale 5.1: n-butyllithium / tetrahydrofuran; toluene; hexane / 1 h / -78 °C / Inert atmosphere; Industrial scale 5.2: 14 h / -78 - 40 °C / Industrial scale View Scheme |
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