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LIDE PHARMACEUTICALS LIMITED

LIDE PHARMACEUTICALS LIMITED is a professional chemicals and APIs leading manufacturer in China. Our core business line covers APIs, Intermediates, Herb extract, etc.

Henan Tianfu Chemical Co., Ltd.

Competitive Price High Quality Fast Delivery custom-made Welcome to Henan Tianfu Chemical Co., Ltd. website. Our company engages in Sodium Tripolyphosphate (STPP) and Sodium Hexametabphosphate (SHMP) production; development of noble me

Dayang Chem (Hangzhou) Co.,Ltd.

As a leading manufacturer and supplier of chemicals in China, DayangChem not only supply popular chemicals, but also DayangChem’s R&D center offer custom synthesis according to the contract research and development services for the fine chemicals, ph

Methyl 1-c-[3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methylphenyl]-alpha-D-glucopyranoside

Cas:1358581-37-9

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Henan Wentao Chemical Product Co., Ltd.

Henan Wentao Chemical Product Co.,Ltd is Located in Zhengzhou High-tech Development Zone with import and export license, We passed ISO 9001:2008 as well, Henan Wentao has developed more than 1000 compounds, which are widely used in the fields of prod

Triumph International Development Limilted

Appearance: Yellowish Powder Storage:Store in cool and dry palce Package:As customer request Application:Used for research and industrial manufacture. Inorganic Chemicals Transportation:Common products:Sea/Air/Courier

Afine Chemicals Limited

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

Hangzhou J&H Chemical Co., Ltd.

J&H CHEM 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. J&H CHEM has some Manufacturing base in Jia

Wuhan Xinhao Biotechnology Co., Ltd.

1. We can provide customers with "one-stop"packaging service,from research,development,production,export and so on 2. Powerful R&D strength let our technology in a leading level,forever,in turn,to provide customers with better service .

Zibo Hangyu Biotechnology Development Co., Ltd

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

Hangzhou Huarong Pharm Co., Ltd.

Hangzhou Huarong Pharm Co., Ltd.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. Hu

Suzhou Health Chemicals Co., Ltd.

High quality,stable supply chain.Appearance:white/off-white or light yellow Storage:Store in cool and dry place, keep away from strong light and heat. Package:aluminum bottle,glass bottle,PTFE bottle,cardboard drum Application:This product can be use

Methyl 1-C-[3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methylphenyl]-alpha-D-glucopyranoside

Cas:1358581-37-9

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

HANGZHOU YUNUO CHEMICAL CO.,LTD

Superior quality, moderate price & quick delivery. Appearance:white crystalline powder Storage:Stored in cool, dry and ventilation place; Away from fire and heat Package:25kg/drum;200kg/drum as per your request Application:It is an important ra

Antimex Chemical Limied

factory?direct?sale Application:healing drugs

Enke Pharma-tech Co.,Ltd. (Cangzhou, China )

high purity Storage:normal temperature Package:DRUM Application:mainly for medical use for R&Dpurpose use only Transportation:AIR,SEA Port:BEIJING,SHANGHAI,TIANJIN,SHENZHEN

Methyl 1-C-[3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methylphenyl]-alpha-D-glucopyranoside

Cas:1358581-37-9

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Guangdong Juda Chemical Industrial Co.,Limited

Appearance:solid or liquid Storage:sealed in cool and dry place Package:As customer's requested Application:Pharma Intermediate Transportation:by courier/air/sea Port:Any port in China

Wuhan Circle Star Chem-medical Technology co.,Ltd.

good quality, competitive price, thoughtful after sale serviceAppearance:white powder Storage:Keep it in dry,shady and cool place Package:25kg,50kg,180kg,200kg,250kg,1000kg,customization Application:Pharma;Industry;Agricultural;chemical reaserch Tran

Henan Kanbei Chemical Co.,LTD

factory?direct?saleAppearance:White powder Storage:Sealed and preserved Package:200/Kilograms Application:healing drugs Transportation:By sea Port:Shanghai/tianjin

Shanghai Chinqesen Biotechnology Co., Ltd.

Good Quality Package:1kg/bag Application:Medical or chemical Transportation:Air/Train/Sea Port:Shenzhen

1358581-37-9

Cas:1358581-37-9

Min.Order:0

Negotiable

Type:Trading Company

inquiry

Chemsigma International Co.,Ltd.

bulk?production Application:Pharmaceutical intermediates

ZHEJIANG JIUZHOU CHEM CO.,LTD

factory?direct?saleAppearance:White powder Storage:Sealed and preserved Package:200/Kilograms Application:healing drugs Transportation:By sea Port:Shanghai/tianjin

LEAP CHEM Co., Ltd.

Best Seller, High Quality, Competitive Price, Fast Delivery, Quick ResponseAppearance:powder, or liquid Storage:Stored in room temperature, ventilated place Package:Bottle, barrel, cargo, container, etc. Application:Pharmaceuticals, intermediates, AP

Canagliflozin 1-methoxy

Cas:1358581-37-9

Min.Order:0

Negotiable

Type:Trading Company

inquiry

Shanghai Rochi Pharmaceutical Co., Ltd.

Shanghai Rochi Pharmaceutical Co., Ltd. is located in Shanghai Zhangjiang Hi-Tech Biological and Pharmaceutical Innovation Park. It is a high-tech enterprise integrating R&D, production and sales of APIs and intermediates. The company's pro

Methyl 1-C-[3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methylphenyl]-alpha-D-glucopyranoside

Cas:1358581-37-9

Min.Order:500 Gram

Negotiable

Type:Manufacturers

inquiry

Changzhou Extraordinary Pharmatech co.,LTD

Changzhou Extraordinary Pharmatech co., LTD. As a leading chemical manufacturer and supplier in China.DAS authentication is passed.We can provide the popular precursor chemicals, we have our own strong R & D team, have our own laboratories and fa

Changzhou Pesan Chemical Co.,Ltd

Strong R&D strength and team We have a R&D team with around 30 R&D personnel.All of our employees have chemical backgrounds and have worked in the chemical industry for many years.Our laboratory can synthesize target products with wei

Hebei Ruishun Trade Co.,Ltd

Superiority 1.We have more than 10 years experience in this area. 2.We could offer you competitive prices with satisfied quality. 3.Our company provides after-sale service and technical assistance as the customers requirements. 4.As first c

Methyl 1-C-[3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methylphenyl]-alpha-D-glucopyranoside

Cas:1358581-37-9

Min.Order:10 Gram

FOB Price: $4.0

Type:Trading Company

inquiry

Reliable Pharmatech (Tianjin) Co., Ltd.

This product is manufactured in commercial scale, with Perfect quality and Competitive price Expert in pharmaceutical technology Professional service in technic, documentation, export, etc. Steady and continuous supply chain Reliable Pharma

Shanghai Yingrui Biopharma Co., Ltd

1. factory price 2. high purity 3.DMF files 4. in stock 5. good service 6. we also provide the custom synthesis service 7. fast delivery SHANGHAI YINGRUI CHEMICAL TECHNOLOGY CO.,LTD. was established in 2009 ,is a research and developmen

1358581-37-9 Canagliflozin intermediates factory

Cas:1358581-37-9

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Synthetic route

methanol
67-56-1

methanol

(2R,3S,4R,5R)-1-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-2,3,4,5,6-pentahydroxyhexan-1-one

(2R,3S,4R,5R)-1-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-2,3,4,5,6-pentahydroxyhexan-1-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
1358581-37-9

(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
ConditionsYield
With methanesulfonic acid Large scale;96.6%
With methanesulfonic acid at 15℃; for 3h; Industrial scale;
methanol
67-56-1

methanol

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one
32469-28-6, 55515-28-1, 55515-29-2, 32384-65-9

(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
1358581-37-9

(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
ConditionsYield
Stage #1: 3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methylphenyl bromide With n-butyllithium In tetrahydrofuran; hexane; toluene at -78℃; 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; hexane; toluene at -78℃; for 3h;
Stage #3: methanol With methanesulfonic acid In tetrahydrofuran; hexane; toluene at -78 - 40℃; for 10h;
83%
2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

C70H82O6Si4

C70H82O6Si4

(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
1358581-37-9

(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
ConditionsYield
With sec.-butyllithium In tetrahydrofuran; hexane; toluene at -78 - -65℃; for 2h; Inert atmosphere;77.8%
methanesulfonic acid
75-75-2

methanesulfonic acid

C36H56FO6SSi4(1-)*Li(1+)

C36H56FO6SSi4(1-)*Li(1+)

(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
1358581-37-9

(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
ConditionsYield
In methanol at 20℃; for 10h;77.6%
methanesulfonic acid
75-75-2

methanesulfonic acid

(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)
898566-17-1

(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
32469-28-6, 55515-28-1, 55515-29-2, 32384-65-9

(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
1358581-37-9

(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
ConditionsYield
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%
methanesulfonic acid
75-75-2

methanesulfonic acid

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one
32469-28-6, 55515-28-1, 55515-29-2, 32384-65-9

(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
1358581-37-9

(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
ConditionsYield
Stage #1: 3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methylphenyl bromide; (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 -100 - -90℃; for 1h; Inert atmosphere;
Stage #2: methanesulfonic acid In tetrahydrofuran; methanol; hexane; toluene at -100 - 20℃;
77%
2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

C18H42O6Si4

C18H42O6Si4

(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
1358581-37-9

(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
ConditionsYield
With tert.-butyl lithium In tetrahydrofuran; toluene; pentane at -78 - -65℃; for 2h; Inert atmosphere;76.7%
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)
898566-17-1

(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)

toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one
32469-28-6, 55515-28-1, 55515-29-2, 32384-65-9

(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
1358581-37-9

(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
ConditionsYield
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%
methanesulfonic acid
75-75-2

methanesulfonic acid

(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)
898566-17-1

(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)

2,3,4,6-tetra-O-acetyl-D-glucono-1,5-lactone
61259-48-1, 73322-42-6

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
1358581-37-9

(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
ConditionsYield
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%
methanesulfonic acid
75-75-2

methanesulfonic acid

(5-bromo-2-chloro-phenyl)-[5-(4-fluorophenyl)-2-thienyl]methanone
1358581-35-7

(5-bromo-2-chloro-phenyl)-[5-(4-fluorophenyl)-2-thienyl]methanone

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one
32469-28-6, 55515-28-1, 55515-29-2, 32384-65-9

(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
1358581-37-9

(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
ConditionsYield
Stage #1: (5-bromo-2-chloro-phenyl)-[5-(4-fluorophenyl)-2-thienyl]methanone With n-butyllithium In tetrahydrofuran; hexane at -78℃; 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; hexane at -78℃; for 2h;
Stage #3: methanesulfonic acid In tetrahydrofuran; methanol; hexane at 20℃; for 16h;
36.7%
5-bromo-2-chlorobenzoic acid
21739-92-4

5-bromo-2-chlorobenzoic acid

(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
1358581-37-9

(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
ConditionsYield
Multi-step reaction with 3 steps
1.1: thionyl chloride / toluene; N,N-dimethyl-formamide / 5 h / 0 - 100 °C
2.1: aluminum (III) chloride / dichloromethane / 16.5 h / -10 - 20 °C
3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C
3.2: 2 h / -78 °C
3.3: 16 h / 20 °C
View Scheme
4-fluoroboronic acid
1765-93-1

4-fluoroboronic acid

(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
1358581-37-9

(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
ConditionsYield
Multi-step reaction with 3 steps
1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / Dimethyl ether; water / 0.5 h / 100 °C / Microwave irradiation
2.1: aluminum (III) chloride / dichloromethane / 16.5 h / -10 - 20 °C
3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C
3.2: 2 h / -78 °C
3.3: 16 h / 20 °C
View Scheme
Multi-step reaction with 5 steps
1.1: tetrabutylammomium bromide; palladium diacetate; potassium carbonate / water / 2 h / 20 °C
2.1: sodium tetrahydroborate; ethanol / 6 h / 20 °C
3.1: thionyl chloride / 3 h / 70 °C
4.1: aluminum (III) chloride / ethyl acetate / 8 h / 80 °C / Cooling with ice
5.1: n-butyllithium / tetrahydrofuran; toluene; hexane / 1 h / -78 °C
5.2: 3 h / -78 °C
5.3: 10 h / -78 - 40 °C
View Scheme
2-(4-fluorophenyl)thiophene
58861-48-6

2-(4-fluorophenyl)thiophene

(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
1358581-37-9

(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
ConditionsYield
Multi-step reaction with 2 steps
1.1: aluminum (III) chloride / dichloromethane / 16.5 h / -10 - 20 °C
2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C
2.2: 2 h / -78 °C
2.3: 16 h / 20 °C
View Scheme
5-bromo-2-chloro-benzoyl chloride
21900-52-7

5-bromo-2-chloro-benzoyl chloride

(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
1358581-37-9

(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
ConditionsYield
Multi-step reaction with 2 steps
1.1: aluminum (III) chloride / dichloromethane / 16.5 h / -10 - 20 °C
2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C
2.2: 2 h / -78 °C
2.3: 16 h / 20 °C
View Scheme
D-glucono-1,4-lactone
1198-69-2

D-glucono-1,4-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
1358581-37-9

(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
ConditionsYield
Multi-step reaction with 2 steps
1: 4-methyl-morpholine / tetrahydrofuran / 1 h / -10 - 45 °C
2: tert.-butyl lithium / tetrahydrofuran; toluene; pentane / 2 h / -78 - -65 °C / Inert atmosphere
View Scheme
methanol
67-56-1

methanol

C36H56FO6SSi4(1-)*Li(1+)

C36H56FO6SSi4(1-)*Li(1+)

(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
1358581-37-9

(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
ConditionsYield
With hydrogenchloride In 2-methyltetrahydrofuran; hexane; toluene at -10 - -5℃; for 2h; Inert atmosphere;25 g
(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one
32469-28-6, 55515-28-1, 55515-29-2, 32384-65-9

(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
1358581-37-9

(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
ConditionsYield
Multi-step reaction with 2 steps
1: n-butyllithium / toluene / -18 - -5 °C
2: methanol / 0 - 20 °C
View Scheme
2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

(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
1358581-37-9

(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
ConditionsYield
Multi-step reaction with 2 steps
1: n-butyllithium / toluene / -18 - -5 °C
2: methanol / 0 - 20 °C
View Scheme
methanesulfonic acid
75-75-2

methanesulfonic acid

1-[1-hydroxy-2,3,4,6-tetra-O-(trimethylsilyl)-β-D-glucopyranosyl]-4-methyl-3-[[5-(4-fluorophenyl)-2-thienyl]methyl]benzene
1132832-76-8

1-[1-hydroxy-2,3,4,6-tetra-O-(trimethylsilyl)-β-D-glucopyranosyl]-4-methyl-3-[[5-(4-fluorophenyl)-2-thienyl]methyl]benzene

(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
1358581-37-9

(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
ConditionsYield
In methanol at 0 - 20℃;
5-iodo-2-methylbenzoic acid
54811-38-0

5-iodo-2-methylbenzoic acid

(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
1358581-37-9

(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
ConditionsYield
Multi-step reaction with 5 steps
1.1: N,N-dimethyl-formamide; thionyl chloride / chlorobenzene / 4 h / 65 - 70 °C / Inert atmosphere; Industrial scale
2.1: aluminum (III) chloride / chlorobenzene / 4 h / 50 - 55 °C / Industrial scale
3.1: aluminum (III) chloride; 1,1,3,3-Tetramethyldisiloxane / chlorobenzene / 10 - 50 °C / Industrial scale
4.1: n-butyllithium / tetrahydrofuran; toluene; hexane / -50 °C
4.2: 3 h / 0 °C
5.1: methanesulfonic acid / 3 h / 15 °C / Industrial scale
View Scheme
Multi-step reaction with 5 steps
1.1: N,N-dimethyl-formamide; thionyl chloride / chlorobenzene / 4 h / 65 - 70 °C / Inert atmosphere; Industrial scale
2.1: aluminum (III) chloride / chlorobenzene / 4 h / 50 - 55 °C / Industrial scale
3.1: aluminum (III) chloride; 1,1,3,3-Tetramethyldisiloxane / chlorobenzene / 10 - 50 °C / Industrial scale
4.1: n-butyllithium / tetrahydrofuran; toluene; hexane / -70 °C / Industrial scale
4.2: 3 h / 0 °C / Industrial scale
5.1: methanesulfonic acid / 3 h / 15 °C / Industrial scale
View Scheme
5-iodo-2-methylbenzoyl chloride
108440-70-6

5-iodo-2-methylbenzoyl chloride

(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
1358581-37-9

(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
ConditionsYield
Multi-step reaction with 4 steps
1.1: aluminum (III) chloride / chlorobenzene / 4 h / 50 - 55 °C / Industrial scale
2.1: aluminum (III) chloride; 1,1,3,3-Tetramethyldisiloxane / chlorobenzene / 10 - 50 °C / Industrial scale
3.1: n-butyllithium / tetrahydrofuran; toluene; hexane / -50 °C
3.2: 3 h / 0 °C
4.1: methanesulfonic acid / 3 h / 15 °C / Industrial scale
View Scheme
Multi-step reaction with 4 steps
1.1: aluminum (III) chloride / chlorobenzene / 4 h / 50 - 55 °C / Industrial scale
2.1: aluminum (III) chloride; 1,1,3,3-Tetramethyldisiloxane / chlorobenzene / 10 - 50 °C / Industrial scale
3.1: n-butyllithium / tetrahydrofuran; toluene; hexane / -70 °C / Industrial scale
3.2: 3 h / 0 °C / Industrial scale
4.1: methanesulfonic acid / 3 h / 15 °C / Industrial scale
View Scheme
(5-(4-fluorophenyl)thiophen-2-yl)(5-iodo-2-methylphenyl)methanone

(5-(4-fluorophenyl)thiophen-2-yl)(5-iodo-2-methylphenyl)methanone

(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
1358581-37-9

(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
ConditionsYield
Multi-step reaction with 3 steps
1.1: aluminum (III) chloride; 1,1,3,3-Tetramethyldisiloxane / chlorobenzene / 10 - 50 °C / Industrial scale
2.1: n-butyllithium / tetrahydrofuran; toluene; hexane / -50 °C
2.2: 3 h / 0 °C
3.1: methanesulfonic acid / 3 h / 15 °C / Industrial scale
View Scheme
Multi-step reaction with 3 steps
1.1: aluminum (III) chloride; 1,1,3,3-Tetramethyldisiloxane / chlorobenzene / 10 - 50 °C / Industrial scale
2.1: n-butyllithium / tetrahydrofuran; toluene; hexane / -70 °C / Industrial scale
2.2: 3 h / 0 °C / Industrial scale
3.1: methanesulfonic acid / 3 h / 15 °C / Industrial scale
View Scheme
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)
898566-17-1

(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)

(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
1358581-37-9

(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
ConditionsYield
Multi-step reaction with 2 steps
1.1: n-butyllithium / tetrahydrofuran; toluene; hexane / -70 °C / Industrial scale
1.2: 3 h / 0 °C / Industrial scale
2.1: methanesulfonic acid / 3 h / 15 °C / Industrial scale
View Scheme
5-bromo-2-thiophencarboxaldehyde
4701-17-1

5-bromo-2-thiophencarboxaldehyde

(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
1358581-37-9

(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
ConditionsYield
Multi-step reaction with 5 steps
1.1: tetrabutylammomium bromide; palladium diacetate; potassium carbonate / water / 2 h / 20 °C
2.1: sodium tetrahydroborate; ethanol / 6 h / 20 °C
3.1: thionyl chloride / 3 h / 70 °C
4.1: aluminum (III) chloride / ethyl acetate / 8 h / 80 °C / Cooling with ice
5.1: n-butyllithium / tetrahydrofuran; toluene; hexane / 1 h / -78 °C
5.2: 3 h / -78 °C
5.3: 10 h / -78 - 40 °C
View Scheme
5-(4-fluorophenyl)thiophene-2-carboxaldehyde
249504-38-9

5-(4-fluorophenyl)thiophene-2-carboxaldehyde

(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
1358581-37-9

(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
ConditionsYield
Multi-step reaction with 4 steps
1.1: sodium tetrahydroborate; ethanol / 6 h / 20 °C
2.1: thionyl chloride / 3 h / 70 °C
3.1: aluminum (III) chloride / ethyl acetate / 8 h / 80 °C / Cooling with ice
4.1: n-butyllithium / tetrahydrofuran; toluene; hexane / 1 h / -78 °C
4.2: 3 h / -78 °C
4.3: 10 h / -78 - 40 °C
View Scheme
[5-(4-fluorophenyl)thiophen-2-yl]methanol
1225916-69-7

[5-(4-fluorophenyl)thiophen-2-yl]methanol

(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
1358581-37-9

(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
ConditionsYield
Multi-step reaction with 3 steps
1.1: thionyl chloride / 3 h / 70 °C
2.1: aluminum (III) chloride / ethyl acetate / 8 h / 80 °C / Cooling with ice
3.1: n-butyllithium / tetrahydrofuran; toluene; hexane / 1 h / -78 °C
3.2: 3 h / -78 °C
3.3: 10 h / -78 - 40 °C
View Scheme
2-chloromethyl-5-(4-fluorophenyl)thiophene

2-chloromethyl-5-(4-fluorophenyl)thiophene

(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
1358581-37-9

(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
ConditionsYield
Multi-step reaction with 2 steps
1.1: aluminum (III) chloride / ethyl acetate / 8 h / 80 °C / Cooling with ice
2.1: n-butyllithium / tetrahydrofuran; toluene; hexane / 1 h / -78 °C
2.2: 3 h / -78 °C
2.3: 10 h / -78 - 40 °C
View Scheme
methanol
67-56-1

methanol

1-[1-hydroxy-2,3,4,6-tetra-O-(trimethylsilyl)-β-D-glucopyranosyl]-4-methyl-3-[[5-(4-fluorophenyl)-2-thienyl]methyl]benzene
1132832-76-8

1-[1-hydroxy-2,3,4,6-tetra-O-(trimethylsilyl)-β-D-glucopyranosyl]-4-methyl-3-[[5-(4-fluorophenyl)-2-thienyl]methyl]benzene

(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
1358581-37-9

(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
ConditionsYield
With methanesulfonic acid at -30 - 20℃; Reagent/catalyst; Temperature;54.9 g
2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one
32469-28-6, 55515-28-1, 55515-29-2, 32384-65-9

(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
1358581-37-9

(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
ConditionsYield
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
(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
1358581-37-9

(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

canagliflozin
842133-18-0

canagliflozin

Conditions
ConditionsYield
With triethylsilane; boron trifluoride diethyl etherate In dichloromethane at -40 - 0℃; for 3h;90%
Stage #1: (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 With aluminum (III) chloride In dichloromethane; acetonitrile at -5℃; for 0.5h;
Stage #2: With triethylsilane In dichloromethane; acetonitrile at -5 - 10℃; for 2h;
79%
With triethylsilane; acetonitrile boron trifluoride complex In n-heptane at -5 - 5℃; for 5h;77.5%
(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
1358581-37-9

(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

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

(2S,3R,4S,5S,6R)-6-[(tertbutyl(dimethyl)silyl)oxymethyl]-2-[3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methyl-phenyl]-2-methoxy-tetrahydropyran-3,4,5-triol
1358581-40-4

(2S,3R,4S,5S,6R)-6-[(tertbutyl(dimethyl)silyl)oxymethyl]-2-[3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methyl-phenyl]-2-methoxy-tetrahydropyran-3,4,5-triol

Conditions
ConditionsYield
With pyridine; dmap for 16h;89.7%

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