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Dayang Chem (Hangzhou) Co.,Ltd.

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

Ipragliflozin

Cas:761423-87-4

Min.Order:1 Gram

FOB Price: $1.0 / 2.0

Type:Lab/Research institutions

inquiry

Hangzhou Hysen Pharma co.,Ltd.

We can provide high quality,cheap price,spot supply and good service. If you have any questions,pls do not hesitate to contact us. Hangzhou Hysen pharma CO.,LTD. is a professional Pharmaceutical company. We are specialized in manufacturing and

Ipragliflozin CAS761423-87-4

Cas:761423-87-4

Min.Order:10 Gram

Negotiable

Type:Lab/Research institutions

inquiry

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

Cangzhou Enke Pharma Tech Co.,ltd. is located in Cangzhou City, Hebei province ,where is a famous petroleum chemical industry city in China. Enke Pharma a high-tech enterprise ,and we are dedicated to developing and manufacturing new ap

Ipragliflozin

Cas:761423-87-4

Min.Order:1 Kilogram

FOB Price: $1.0

Type:Manufacturers

inquiry

Chemwill Asia Co., Ltd.

Our main production base is located in Xuzhou industry park. We are certified both to the ISO 9001 and ISO 14001 Standards, have a safety management system in place.Our R&D team masters core technology for process-design of target building block

Ipragliflozin

Cas:761423-87-4

Min.Order:5 Kiloliter

FOB Price: $1.2 / 5.0

Type:Manufacturers

inquiry

Hebei Nengqian Chemical Import and Export Co., LTD

With our good experience, we offer detailed technical support and advice to assist customers. We communicate closely with customers to establish their quality requirements. Consistent Quality Our plant has strict quality control in each manufacturin

CAS 761423-87-4 Ipragliflozin

Cas:761423-87-4

Min.Order:1 Kilogram

FOB Price: $10.0 / 16.0

Type:Trading Company

inquiry

Zhuozhou Wenxi import and Export Co., Ltd

WITH US,YOUR MONEY IN SAFE,YOUR BUSINESS IN SAFE 1)Quick Response Within 12 hours; 2)Quality Guarantee: All products are strictly tested by our QC, confirmed by QA and approved by third party lab in China, USA, Canada, Germany, UK, Italy, France et

New production CAS 761423-87-4 with best quality

Cas:761423-87-4

Min.Order:1 Kilogram

FOB Price: $139.0 / 210.0

Type:Trading Company

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Wuhan Han Sheng New Material Technology Co.,Ltd

Our Advantage: high quality with competitive price High quality standard: BP/USP/EP Enterprise standard All purity customized Fast and safe delivery We have reliable forwarder who can help us deliver our goods more fast and safe. We

Ipragliflozin/High quality/Best price/In stock

Cas:761423-87-4

Min.Order:10 Kilogram

Negotiable

Type:Trading Company

inquiry

Hubei Langyou International Trading Co., Ltd

Advantages: Hubei XinRunde Chemical Co., Ltd is a renowned pharmaceutical manufacturer. We can offer high quality products at competitive price in quick delivery with 100% custom pass guaranteed. Never stop striving to offer our best serv

Lglese Manufacturer For Lglegide Intermediates

Cas:761423-87-4

Min.Order:10 Gram

Negotiable

Type:Other

inquiry

Hangzhou Think Chemical Co. Ltd

Ipragliflozin CAS No.:761423-87-4 HANGZHOU THINK CHEMICAL CO., LTD. (THINKCHEM) is an integrative corporation of trade, research and contract manufacture. With about ten years of business experiences on the marketing & distribution, thi

High purity Ipragliflozin CAS No.:761423-87-4

Cas:761423-87-4

Min.Order:1 Kilogram

FOB Price: $2.0

Type:Other

inquiry

Shanghai Upbio Tech Co.,Ltd

1.No Less 8 years exporting experience. Clients can 100% received goods 2.Lower Price with higher quality 3,Free sample 4,We are sincerely responsible for the "product quality" and "After Service" Upbio is Specialized

(1S)-1,5-Anhydro-1-C-[3-[(1-benzothiophen-2-yl)methyl]-4-fluorophenyl]-D-glucitol 761423-87-4

Cas:761423-87-4

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Shanghai Minstar Chemical Co., Ltd

(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

(1S)-1,5-Anhydro-1-C-[3-[(1-benzothiophen-2-yl)methyl]-4-fluorophenyl]-D-glucitol

Cas:761423-87-4

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Qingdao Beluga Import and Export Co., LTD

Ipragliflozin CAS: 761423-87-4 Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating research and development, production and trade of chemical intermediates, specializing in high quality organic intermedi

Ipragliflozin CAS: 761423-87-4

Cas:761423-87-4

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Shandong Hanjiang Chemical Co., Ltd.

Hello, 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

(1S)-1,5-Anhydro-1-C-[3-[(1-benzothiophen-2-yl)methyl]-4-fluorophenyl]-D-glucitol

Cas:761423-87-4

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Triumph International Development Limilted

Appearance: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

Ipragliflozin

Cas:761423-87-4

Min.Order:100 Gram

Negotiable

Type:Lab/Research institutions

inquiry

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

IPRAGLIFLOZIN

Cas:761423-87-4

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

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

Factory Ipragliflozin

Cas:761423-87-4

Min.Order:10 Gram

FOB Price: $100.0

Type:Lab/Research institutions

inquiry

SHANGHAI SYSTEAM BIOCHEM CO., LTD

We 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

Ipragliflozin/High quality/Best price/In stock

Cas:761423-87-4

Min.Order:100 Gram

FOB Price: $100.0 / 2000.0

Type:Lab/Research institutions

inquiry

Siwei Development Group Ltd.

Product 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

Best Quality Ipragliflozin

Cas:761423-87-4

Min.Order:1 Kilogram

Negotiable

Type:Trading Company

inquiry

Hangzhou Huarong Pharm Co., Ltd.

DMF 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

Ipragliflozin

Cas:761423-87-4

Min.Order:1 Kilogram

Negotiable

Type:Trading Company

inquiry

Zibo Dorne chemical technology co. LTD

Product 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,

Ipragliflozin

Cas:761423-87-4

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Henan Wentao Chemical Product Co., Ltd.

We are leading fine chemicals supplier in China with ISO certificate, Our main business covers the fields below: 1.Noble Metal Catalysts (Pt.Pd...) 2.Organic Phosphine Ligands (Tert-butyl-phosphine.Cyclohexyl-phosphine...) 3.OLED

IpragliflozinCAS NO.: 761423-87-4

Cas:761423-87-4

Min.Order:1 Gram

FOB Price: $3.0

Type:Lab/Research institutions

inquiry

Xiamen Jenny Chemical Technology Co., Ltd.

GMP standard, high purity, competitive price, in stock 1. Quick Response: within 6 hours after receiving your email. 2. Quality Guarantee: All products are strictly tested by our QC, confirmed by QA, and approved by a third-party lab in China, USA,

(1S)-1,5-Anhydro-1-C-[3-[(1-benzothiophen-2-yl)methyl]-4-fluorophenyl]-D-glucitol

Cas:761423-87-4

Min.Order:1 Milligram

Negotiable

Type:Trading Company

inquiry

EAST CHEMSOURCES LIMITED

factory?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

Ipragliflozin/High quality/Best price/In stock

Cas:761423-87-4

Min.Order:1 Kilogram

FOB Price: $18.0 / 20.0

Type:Trading Company

inquiry

Shandong Mopai Biotechnology Co., LTD

Shandong Mopai Biotechnology 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 chemicals. W

(1S)-1,5-Anhydro-1-C-[3-[(1-benzothiophen-2-yl)methyl]-4-fluorophenyl]-D-glucitol

Cas:761423-87-4

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

KAISA GROUP INC

1.Applied in food field.it can improve the immune system and prolong life. 2.Appliedin cosmetic field.it can improve the skin care. 3.Applied in pharmaceutical field.it can treat various dieases. 4.Our product quality assurance will make our customer

Ipragliflozin/High quality/Best price/In stock

Cas:761423-87-4

Min.Order:1 Metric Ton

FOB Price: $1.5

Type:Trading Company

inquiry

Nanjing Fred Technology Co.,Ltd.

Ipragliflozin is one of the most competitive products in our company. We can supply it with good quality and best price. Appearance:powder Storage:Refrigerator Package:According to the demand of customer Application:API Port:shanghai

Ipragliflozin--supply from china

Cas:761423-87-4

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Hangzhou Zhongqi chem Co.,Ltd.

Located in Hangzhou National Hi-Tech Industrial Development Zone, zhongqichem is a technical company mainly focus on the Custom synthesis, manufacturing, sales of chemicals to various industries. Benefiting from the outstanding customer service an

Ipragliflozin

Cas:761423-87-4

Min.Order:1 Gram

Negotiable

Type:Other

inquiry

Golden Pharma Co., Limited

GOLDEN PHARMA CO.,LIMITED.is a professional pharmaceutical company,our team have more than 20years expereince in pharmaceutical production and sales. we are a professional technical enterprise specializing in the R & D, production,QA regulation

Ipragliflozin

Cas:761423-87-4

Min.Order:1 Kilogram

Negotiable

Type:Other

inquiry

Bluecrystal chem-union

We are a Union of chemistry in China, consists of chemists,engineers, laboratories,factories in China. We organize surplus capacity of R&D and production as well as custom synthesis for chemical products and chemical business project. We are supp

Ipragliflozin/High quality/Best price/In stock

Cas:761423-87-4

Min.Order:1 Metric Ton

FOB Price: $1.0

Type:Trading Company

inquiry

GIHI CHEMICALS CO.,LIMITED

Lower 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

Ipragliflozin

Cas:761423-87-4

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Synthetic route

(1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-[3-[(1-benzothiophen-2-yl)methyl]-4-fluorophenyl]-D-sorbitol
1034305-21-9

(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
761423-87-4

(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

B

(1R)-1,5-anhydro-1-{3-[(1-benzothiophen-2-yl)methyl]-4-fluorophenyl}-D-glucitol

(1R)-1,5-anhydro-1-{3-[(1-benzothiophen-2-yl)methyl]-4-fluorophenyl}-D-glucitol

Conditions
ConditionsYield
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
1034305-21-9

(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
761423-87-4

(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
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%
(1S)-1,5-anhydro-1-{3-[(1-benzothiophen-2-yl)methyl]-4-fluorophenyl}-2,3,4,6-tetra-O-pivaloyl-D-glucitol

(1S)-1,5-anhydro-1-{3-[(1-benzothiophen-2-yl)methyl]-4-fluorophenyl}-2,3,4,6-tetra-O-pivaloyl-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
761423-87-4

(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
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
761423-01-2

(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
761423-87-4

(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
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;
C25H29FO5S

C25H29FO5S

(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
761423-87-4

(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
With triethylsilane; boron trichloride acetic acid In dichloromethane at -20 - 0℃;71.4%
C24H27FO5S

C24H27FO5S

(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
761423-87-4

(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
With triethylsilane; boron trichloride acetic acid In dichloromethane; acetonitrile at -20 - 0℃;70.2%
1-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-3,4,6-tri-O-tert-butyldimethylsilyl-D-glucal

1-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-3,4,6-tri-O-tert-butyldimethylsilyl-D-glucal

(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
761423-87-4

(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
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
1-(3-(benzo[b]thiophen-2-methyl)-4-fluorophenyl)-3-O-triisopropylsilyl-4,6-O-di-tert-butylsilylene-D-glucal

1-(3-(benzo[b]thiophen-2-methyl)-4-fluorophenyl)-3-O-triisopropylsilyl-4,6-O-di-tert-butylsilylene-D-glucal

(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
761423-87-4

(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
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
1034305-11-7

(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
761423-87-4

(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
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
1034305-17-3

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
761423-87-4

(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
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
93777-26-5

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
761423-87-4

(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
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
95-15-8

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
761423-87-4

(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
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
318967-97-4

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
761423-87-4

(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
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
1198-69-2

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
761423-87-4

(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
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
C18H42O6Si4

C18H42O6Si4

(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
761423-87-4

(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
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
1034305-17-3

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
761423-87-4

(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

B

(1R)-1,5-anhydro-1-{3-[(1-benzothiophen-2-yl)methyl]-4-fluorophenyl}-D-glucitol

(1R)-1,5-anhydro-1-{3-[(1-benzothiophen-2-yl)methyl]-4-fluorophenyl}-D-glucitol

Conditions
ConditionsYield
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
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

A

(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
761423-87-4

(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

B

(1R)-1,5-anhydro-1-{3-[(1-benzothiophen-2-yl)methyl]-4-fluorophenyl}-D-glucitol

(1R)-1,5-anhydro-1-{3-[(1-benzothiophen-2-yl)methyl]-4-fluorophenyl}-D-glucitol

Conditions
ConditionsYield
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
81058-27-7

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
761423-87-4

(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
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
(2R,3R,4S,5R,6R)-2-chloro-6-(pivaloyloxymethyl)tetrahydro-2H-pyran-3,4,5-triyl tris(2,2-dimethylpropanoate)

(2R,3R,4S,5R,6R)-2-chloro-6-(pivaloyloxymethyl)tetrahydro-2H-pyran-3,4,5-triyl tris(2,2-dimethylpropanoate)

(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
761423-87-4

(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
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
2-[(5-iodo-2-fluorophenyl)methyl]-1-benzothiophene

2-[(5-iodo-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
761423-87-4

(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
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
604-68-2

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
761423-87-4

(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
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
572-09-8

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
761423-87-4

(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
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
61403-85-8

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
761423-87-4

(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
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
4196-35-4

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
761423-87-4

(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
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
492-62-6

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
761423-87-4

(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
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
1-phenylsulfonyl-3,4,6-tri-O-tert-butyldimethylsilyl-D-glucal

1-phenylsulfonyl-3,4,6-tri-O-tert-butyldimethylsilyl-D-glucal

(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
761423-87-4

(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
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
C36H72O7SSi4

C36H72O7SSi4

(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
761423-87-4

(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
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
C36H72O5SSi4

C36H72O5SSi4

(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
761423-87-4

(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
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
3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenylboronic acid pinacol ester

3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenylboronic acid pinacol ester

(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
761423-87-4

(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
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
761423-87-4

(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
147-85-3

L-proline

Ipragliflozin L-proline
951382-34-6

Ipragliflozin L-proline

Conditions
ConditionsYield
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
761423-87-4

(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
98-59-9

p-toluenesulfonyl chloride

((2R,3S,4R,5R,6S)-6-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)methyl 4-methylbenzenesulfonate

((2R,3S,4R,5R,6S)-6-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)methyl 4-methylbenzenesulfonate

Conditions
ConditionsYield
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
761423-87-4

(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

(2S,3S,5R,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-3,5-dihydroxy-6-(hydroxymethyl)dihydro-2H-pyran-4(3H)-one

(2S,3S,5R,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-3,5-dihydroxy-6-(hydroxymethyl)dihydro-2H-pyran-4(3H)-one

Conditions
ConditionsYield
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
761423-87-4

(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

(2S,3R,4S,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-methyltetrahydro-2H-pyran-3,4,5-triol

(2S,3R,4S,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-methyltetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
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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