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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

Methyl 1-C-[4-chloro-3-[[4-[[(3S)-tetrahydro-3-furanyl]oxy]phenyl]methyl]phenyl]-alpha-D-glucopyranoside

Cas:1279691-36-9

Min.Order:1 Kilogram

FOB Price: $1.0

Type:Lab/Research institutions

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Hangzhou Think Chemical Co. Ltd

Methyl 1-C-[4-chloro-3-[[4-[[(3S)-tetrahydro-3-furanyl]oxy]phenyl]methyl]phenyl]-alpha-D-glucopyranoside CAS1279691-36-9 HANGZHOU THINK CHEMICAL CO., LTD. (THINKCHEM) is an integrative corporation of trade, research and contract manufacture.

Ality Chemical Corporation

The 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

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

Methyl 1-c-[4-chloro-3-[[4-[[(3S)-tetrahydro-3-furanyl]oxy]phenyl]methyl]phenyl]-alpha-D-glucopyranoside

Cas:1279691-36-9

Min.Order:1 Kilogram

FOB Price: $2.0

Type:Lab/Research institutions

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

Methyl 1-C-{4-chloro-3-{{4-{[(3S)-tetrahydro-3-furanyl]-oxy}-phenyl}-methyl}-phenyl}-α-D-glucopyranoside

Cas:1279691-36-9

Min.Order:5 Kiloliter

FOB Price: $1.2 / 5.0

Type:Manufacturers

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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

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

Pharmaceutical Grade CAS 1279691-36-9 with competitive price

Cas:1279691-36-9

Min.Order:1 Kilogram

FOB Price: $139.0 / 210.0

Type:Trading Company

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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

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

Hangzhou Huarong Pharm Co., Ltd.

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, development and manufac

Qingdao Beluga Import and Export Co., LTD

(2S,3R,4S,5S,6R)-2-(3-(4-((S)-tetrahydrofuran-3-yloxy)benzyl)-4-chlorophenyl)-tetrahydro-6-(hydroxyMethyl)-2-Methoxy-2H-pyran-3,4,5-triol CAS:1279691-36-9 Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrat

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: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

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

SHANGHAI T&W PHARMACEUTICAL CO., LTD.

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

Chemlyte Solutions

Chemlyte Solutions believe that customers and suppliers deserve much more than what traditional distributors can offer. To grow in today s fast-paced and increasingly competitive market it is essential to be able to quickly adapt to market forces eff

Shanghai Massive Chemical Technology Co., Ltd.

Massive Chemical is certified with ISO9001 and ISO14001 manufacturer for this product. We will offer all documents as requirement for the materials which includes, Certificate of Analysis, Material Safety Data Sheet, and Method of Analysis and

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

Siwei Development Group Ltd.

Product name: Methyl 1-C-[4-Chloro-3-[[4-[[(3S)-Tetrahydro-3-Furanyl]Oxy]Phenyl]Methyl]Phenyl]-Alpha-D-Glucopyranoside CAS No.:1279691-36-9 Molecule Formula:C24H29ClO8 Molecule Weight:480.93 Purity: 99% Package: 25kg/drum Description:White powd

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,

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

Empagliflozin Intermediate CAS 1279691-36-9 CAS NO.1279691-36-9

Cas:1279691-36-9

Min.Order:1 Metric Ton

FOB Price: $7.0 / 8.0

Type:Trading Company

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Nanjing Fred Technology Co.,Ltd.

(2S,3R,4S,5S,6R)-2-(3-(4-((S)-tetrahydrofuran-3-yloxy)benzyl)-4-chlorophenyl)-tetrahydro-6-(hydroxyMethyl)-2-Methoxy-2H-pyran-3,4,5-triol is one of the most competitive products in our company. We can supply it with good quality and best price. Appe

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

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

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

HANGZHOU YUNUO CHEMICAL CO.,LTD

Superior quality, moderate price & quick delivery. Appearance:white crystalline powder Storage:Sealed in a cool ,dry and microtherm place , avoid light . Package:25kg/drum;200kg/drum as per your request Application:It is an important raw mater

Wuxi TAA Chemical Industry Co.,LTD.

1.A strong technical force and advanced processing equipments. The quality of the products has been strictly inspected and all kinds of index have reached or exceeded domestic and international standards.2. Now we have established long-term stable re

GIHI CHEMICALS CO.,LIMITED

high purity,in stock Package:25kg/drum,or as per customers'demand Application:API,or Intermediates,fine chemicals Transportation:air,sea,courier

Empagliflozin N-1

Cas:1279691-36-9

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Hangzhou Dingyan Chem Co., Ltd

manufacture Application:The refence standard products, for lab use, also we could produce bigger quantity on yr requirement.

Synthetic route

methanol
67-56-1

methanol

(2S,3R,4S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol
1279691-35-8

(2S,3R,4S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
1279691-36-9

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
With hydrogenchloride In water at 20 - 30℃; for 1h;90.5%
With hydrogenchloride In water at 20℃; pH=0; Product distribution / selectivity;
With trifluoroacetic acid at 20℃; for 5h; Reagent/catalyst; Large scale;10 kg
methanol
67-56-1

methanol

(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene
915095-89-5

(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

(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-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
1279691-36-9

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
Stage #1: (S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)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: methanol With methanesulfonic acid In tetrahydrofuran; hexane; toluene at 0 - 40℃; for 10h; Large scale;
87%
Stage #1: (S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)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; hexane; toluene at -78℃; for 3h; Inert atmosphere; Large scale;
Stage #2: methanol With methanesulfonic acid In tetrahydrofuran; hexane; toluene at 0 - 40℃; for 10h; Inert atmosphere; Large scale;
84%
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene
915095-89-5

(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

(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-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
1279691-36-9

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
Stage #1: (S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene With n-butyllithium In tetrahydrofuran; 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 In tetrahydrofuran; toluene at -78℃; for 3h; Large scale;
Stage #3: With methanesulfonic acid In tetrahydrofuran; methanol; toluene at 0 - 40℃; for 10h; Large scale;
84%
(3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran
915095-94-2

(3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran

C18H42O6Si4

C18H42O6Si4

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
1279691-36-9

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane; toluene at -78 - -65℃; for 2h; Inert atmosphere;77.6%
methanesulfonic acid
75-75-2

methanesulfonic acid

C35H58ClO8Si4(1-)*Li(1+)

C35H58ClO8Si4(1-)*Li(1+)

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
1279691-36-9

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
In methanol at 20℃; for 10h;76.3%
(S)-(2-chloro-5-iodophenyl)(4-((tetrahydrofuran-3-yl)oxy)phenyl)methanone
915095-87-3

(S)-(2-chloro-5-iodophenyl)(4-((tetrahydrofuran-3-yl)oxy)phenyl)methanone

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
1279691-36-9

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: aluminum (III) chloride; 1,1,3,3-Tetramethyldisiloxane / toluene / 2.5 h / 0 - 23 °C
2: isopropylmagnesium chloride; lithium chloride / tetrahydrofuran / 1.5 h / -20 - 10 °C
3: hydrogenchloride / isopropyl alcohol / 5 h / 38 - 42 °C / pH 2
4: hydrogenchloride / isopropyl alcohol; methanol
View Scheme
(3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran
915095-94-2

(3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
1279691-36-9

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: isopropylmagnesium chloride; lithium chloride / tetrahydrofuran / 1.5 h / -20 - 10 °C
2: hydrogenchloride / isopropyl alcohol / 5 h / 38 - 42 °C / pH 2
3: hydrogenchloride / isopropyl alcohol; methanol
View Scheme
Multi-step reaction with 2 steps
1: lithium chloride; isopropylmagnesium chloride / tetrahydrofuran / -30 - -20 °C / Inert atmosphere; Large scale
2: hydrogenchloride / methanol; water / 4 h / 20 °C / Large scale
View Scheme
Multi-step reaction with 2 steps
1.1: TurboGrignard / tetrahydrofuran / 1 h / -30 - -20 °C / Inert atmosphere
1.2: 0.5 h / Inert atmosphere
2.1: hydrogenchloride / water / 1 h / 20 - 30 °C
View Scheme
C35H59ClO8Si4

C35H59ClO8Si4

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
1279691-36-9

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride / isopropyl alcohol / 5 h / 38 - 42 °C / pH 2
2: hydrogenchloride / isopropyl alcohol; methanol
View Scheme
C24H29ClO8

C24H29ClO8

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
1279691-36-9

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
With hydrogenchloride In methanol; isopropyl alcohol204 g
2-chloro-5-iodobenzoic acid
19094-56-5

2-chloro-5-iodobenzoic acid

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
1279691-36-9

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: oxalyl dichloride; N,N-dimethyl-formamide / fluorobenzene / 2 h / 15 - 25 °C
2: aluminum (III) chloride / 1 h / 0 - 25 °C
3: potassium tert-butylate / tetrahydrofuran / 0.5 h / 7 - 10 °C
4: aluminum (III) chloride; 1,1,3,3-Tetramethyldisiloxane / toluene / 2.5 h / 0 - 23 °C
5: isopropylmagnesium chloride; lithium chloride / tetrahydrofuran / 1.5 h / -20 - 10 °C
6: hydrogenchloride / isopropyl alcohol / 5 h / 38 - 42 °C / pH 2
7: hydrogenchloride / isopropyl alcohol; methanol
View Scheme
2-chloro-5-iodobenzoylchloride
281652-58-2

2-chloro-5-iodobenzoylchloride

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
1279691-36-9

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: aluminum (III) chloride / 1 h / 0 - 25 °C
2: potassium tert-butylate / tetrahydrofuran / 0.5 h / 7 - 10 °C
3: aluminum (III) chloride; 1,1,3,3-Tetramethyldisiloxane / toluene / 2.5 h / 0 - 23 °C
4: isopropylmagnesium chloride; lithium chloride / tetrahydrofuran / 1.5 h / -20 - 10 °C
5: hydrogenchloride / isopropyl alcohol / 5 h / 38 - 42 °C / pH 2
6: hydrogenchloride / isopropyl alcohol; methanol
View Scheme
(2-chloro-5-iodophenyl)(4-fluorophenyl)methanone
915095-86-2

(2-chloro-5-iodophenyl)(4-fluorophenyl)methanone

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
1279691-36-9

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 7 - 10 °C
2: aluminum (III) chloride; 1,1,3,3-Tetramethyldisiloxane / toluene / 2.5 h / 0 - 23 °C
3: isopropylmagnesium chloride; lithium chloride / tetrahydrofuran / 1.5 h / -20 - 10 °C
4: hydrogenchloride / isopropyl alcohol / 5 h / 38 - 42 °C / pH 2
5: hydrogenchloride / isopropyl alcohol; methanol
View Scheme
D-glucono-1,4-lactone
1198-69-2

D-glucono-1,4-lactone

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
1279691-36-9

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-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: n-butyllithium / tetrahydrofuran; toluene; hexane / 2 h / -78 - -65 °C / Inert atmosphere
View Scheme
methanol
67-56-1

methanol

(2S,3R,4S,5R,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-ol

(2S,3R,4S,5R,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-ol

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
1279691-36-9

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
With methanesulfonic acid at 40 - 43℃; for 3h; Large scale;4.18 kg
C18H42O6Si4

C18H42O6Si4

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
1279691-36-9

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: lithium chloride; isopropylmagnesium chloride / tetrahydrofuran / -30 - -20 °C / Inert atmosphere; Large scale
2: hydrogenchloride / methanol; water / 4 h / 20 °C / Large scale
View Scheme
(2S,3R,4S,5R,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-ol

(2S,3R,4S,5R,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-ol

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
1279691-36-9

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
With hydrogenchloride In methanol; water at 20℃; for 4h; Large scale;
4-bromo-aniline
106-40-1

4-bromo-aniline

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
1279691-36-9

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: water; methanol / 3.5 h / 20 °C / Cooling with ice; Large scale
2.1: ethyl acetate / 0.5 h / Cooling with ice; Large scale
2.2: 6.5 h / 20 - 75 °C / Cooling with ice; Large scale
3.1: hydrogenchloride / water; ethanol / 8 h / Reflux; Large scale
4.1: hydrogenchloride; sodium nitrite / water / 2 h / -5 - 0 °C / Large scale
4.2: 3 h / 60 °C / Large scale
5.1: potassium tert-butylate / tetrahydrofuran / 1 h / 0 - 10 °C / Inert atmosphere; Large scale
6.1: n-butyllithium / tetrahydrofuran; toluene; hexane / 1 h / -78 °C / Inert atmosphere; Large scale
6.2: 3 h / -78 °C / Large scale
6.3: 10 h / 0 - 40 °C / Large scale
View Scheme
4-bromoacetanilide
103-88-8

4-bromoacetanilide

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
1279691-36-9

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: ethyl acetate / 0.5 h / Cooling with ice; Large scale
1.2: 6.5 h / 20 - 75 °C / Cooling with ice; Large scale
2.1: hydrogenchloride / water; ethanol / 8 h / Reflux; Large scale
3.1: hydrogenchloride; sodium nitrite / water / 2 h / -5 - 0 °C / Large scale
3.2: 3 h / 60 °C / Large scale
4.1: potassium tert-butylate / tetrahydrofuran / 1 h / 0 - 10 °C / Inert atmosphere; 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: 10 h / 0 - 40 °C / Large scale
View Scheme
p-fluorotoluene
352-32-9

p-fluorotoluene

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
1279691-36-9

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: N-Bromosuccinimide; dibenzoyl peroxide / chloroform / 6 h / 70 °C / Large scale
2.1: ethyl acetate / 0.5 h / Cooling with ice; Large scale
2.2: 6.5 h / 20 - 75 °C / Cooling with ice; Large scale
3.1: hydrogenchloride / water; ethanol / 8 h / Reflux; Large scale
4.1: hydrogenchloride; sodium nitrite / water / 2 h / -5 - 0 °C / Large scale
4.2: 3 h / 60 °C / Large scale
5.1: potassium tert-butylate / tetrahydrofuran / 1 h / 0 - 10 °C / Inert atmosphere; Large scale
6.1: n-butyllithium / tetrahydrofuran; toluene; hexane / 1 h / -78 °C / Inert atmosphere; Large scale
6.2: 3 h / -78 °C / Large scale
6.3: 10 h / 0 - 40 °C / Large scale
View Scheme
4-Fluorobenzyl bromide
459-46-1

4-Fluorobenzyl bromide

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
1279691-36-9

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: ethyl acetate / 0.5 h / Cooling with ice; Large scale
1.2: 6.5 h / 20 - 75 °C / Cooling with ice; Large scale
2.1: hydrogenchloride / water; ethanol / 8 h / Reflux; Large scale
3.1: hydrogenchloride; sodium nitrite / water / 2 h / -5 - 0 °C / Large scale
3.2: 3 h / 60 °C / Large scale
4.1: potassium tert-butylate / tetrahydrofuran / 1 h / 0 - 10 °C / Inert atmosphere; 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: 10 h / 0 - 40 °C / Large scale
View Scheme
N-[4-bromo-2-(4-fluorobenzyl)]acetanilide

N-[4-bromo-2-(4-fluorobenzyl)]acetanilide

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
1279691-36-9

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: hydrogenchloride / water; ethanol / 8 h / Reflux; Large scale
2.1: hydrogenchloride; sodium nitrite / water / 2 h / -5 - 0 °C / Large scale
2.2: 3 h / 60 °C / Large scale
3.1: potassium tert-butylate / tetrahydrofuran / 1 h / 0 - 10 °C / Inert atmosphere; Large scale
4.1: n-butyllithium / tetrahydrofuran; toluene; hexane / 1 h / -78 °C / Inert atmosphere; Large scale
4.2: 3 h / -78 °C / Large scale
4.3: 10 h / 0 - 40 °C / Large scale
View Scheme
4-bromo-2-(4-fluorobenzyl)aniline

4-bromo-2-(4-fluorobenzyl)aniline

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
1279691-36-9

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: hydrogenchloride; sodium nitrite / water / 2 h / -5 - 0 °C / Large scale
1.2: 3 h / 60 °C / Large scale
2.1: potassium tert-butylate / tetrahydrofuran / 1 h / 0 - 10 °C / Inert atmosphere; Large scale
3.1: n-butyllithium / tetrahydrofuran; toluene; hexane / 1 h / -78 °C / Inert atmosphere; Large scale
3.2: 3 h / -78 °C / Large scale
3.3: 10 h / 0 - 40 °C / Large scale
View Scheme
4-bromo-2-(4-fluorobenzyl)chlorobenzene

4-bromo-2-(4-fluorobenzyl)chlorobenzene

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
1279691-36-9

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: potassium tert-butylate / tetrahydrofuran / 1 h / 0 - 10 °C / Inert atmosphere; Large scale
2.1: n-butyllithium / tetrahydrofuran; toluene; hexane / 1 h / -78 °C / Inert atmosphere; Large scale
2.2: 3 h / -78 °C / Large scale
2.3: 10 h / 0 - 40 °C / Large scale
View Scheme
o-toluidine
95-53-4

o-toluidine

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
1279691-36-9

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: N-Bromosuccinimide / dichloromethane / 10 h / 5 °C / Cooling with ice; Large scale
2.1: hydrogenchloride; sodium nitrite / water / 3 h / -5 - 0 °C / Large scale
2.2: 3 h / 60 °C / Large scale
3.1: N-Bromosuccinimide; dibenzoyl peroxide / chloroform / 4 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 / 3 h / -78 °C / Inert atmosphere; Large scale
5.2: 10 h / 0 - 40 °C / Inert atmosphere; Large scale
View Scheme
(S)-3-phenoxytetrahydrofuran

(S)-3-phenoxytetrahydrofuran

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
1279691-36-9

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
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 / 3 h / -78 °C / Inert atmosphere; Large scale
2.2: 10 h / 0 - 40 °C / Inert atmosphere; Large scale
View Scheme
Multi-step reaction with 2 steps
1.1: ethyl acetate / 0.5 h / Cooling with ice; Large scale
1.2: 8.5 h / 78 °C / Cooling with ice; Large scale
2.1: n-butyllithium / tetrahydrofuran; toluene / 1 h / -78 °C / Large scale
2.2: 3 h / -78 °C / Large scale
2.3: 10 h / 0 - 40 °C / Large scale
View Scheme
4-Bromo-2-methylaniline
583-75-5

4-Bromo-2-methylaniline

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
1279691-36-9

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: hydrogenchloride; sodium nitrite / water / 3 h / -5 - 0 °C / Large scale
1.2: 3 h / 60 °C / Large scale
2.1: N-Bromosuccinimide; dibenzoyl peroxide / chloroform / 4 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 / 3 h / -78 °C / Inert atmosphere; Large scale
4.2: 10 h / 0 - 40 °C / Inert atmosphere; Large scale
View Scheme
2-chloro-5-bromotoluene
54932-72-8

2-chloro-5-bromotoluene

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
1279691-36-9

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: N-Bromosuccinimide; dibenzoyl peroxide / chloroform / 4 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 / 3 h / -78 °C / Inert atmosphere; Large scale
3.2: 10 h / 0 - 40 °C / Inert atmosphere; Large scale
View Scheme
5-Bromo-2-chlorobenzyl bromide
149965-41-3

5-Bromo-2-chlorobenzyl bromide

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
1279691-36-9

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
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 / 3 h / -78 °C / Inert atmosphere; Large scale
2.2: 10 h / 0 - 40 °C / Inert atmosphere; Large scale
View Scheme
fluorobenzene
462-06-6

fluorobenzene

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
1279691-36-9

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: potassium tert-butylate / tetrahydrofuran; tert-butyl alcohol / 1.5 h / 0 - 10 °C / Inert atmosphere; 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 / 3 h / -78 °C / Inert atmosphere; Large scale
3.2: 10 h / 0 - 40 °C / Inert atmosphere; Large scale
View Scheme
Multi-step reaction with 3 steps
1.1: potassium tert-butylate / tetrahydrofuran / 1 h / 0 - 10 °C / Inert atmosphere; Large scale
2.1: ethyl acetate / 0.5 h / Cooling with ice; Large scale
2.2: 8.5 h / 78 °C / Cooling with ice; Large scale
3.1: n-butyllithium / tetrahydrofuran; toluene / 1 h / -78 °C / Large scale
3.2: 3 h / -78 °C / Large scale
3.3: 10 h / 0 - 40 °C / Large scale
View Scheme
4-bromo-1-chloro-2-(chloromethyl)benzene

4-bromo-1-chloro-2-(chloromethyl)benzene

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
1279691-36-9

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: ethyl acetate / 0.5 h / Cooling with ice; Large scale
1.2: 8.5 h / 78 °C / Cooling with ice; Large scale
2.1: n-butyllithium / tetrahydrofuran; toluene / 1 h / -78 °C / Large scale
2.2: 3 h / -78 °C / Large scale
2.3: 10 h / 0 - 40 °C / Large scale
View Scheme
(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
1279691-36-9

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

1-C-[4-chloro-3-[[4-[[(3S)-tetrahydro-3-furanyl]oxy]phenyl]methyl]phenyl]-D-glucopyranoside
1417573-74-0

1-C-[4-chloro-3-[[4-[[(3S)-tetrahydro-3-furanyl]oxy]phenyl]methyl]phenyl]-D-glucopyranoside

Conditions
ConditionsYield
With triethylsilane; aluminum (III) chloride In dichloromethane; acetonitrile at 13 - 20℃; for 5h; Inert atmosphere; Cooling with ice;96.25%
(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
1279691-36-9

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

acetic anhydride
108-24-7

acetic anhydride

(2S,3R,4S,5R,6R)-6-(acetoxymethyl)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triyl triacetate

(2S,3R,4S,5R,6R)-6-(acetoxymethyl)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triyl triacetate

Conditions
ConditionsYield
With dmap; triethylamine In tetrahydrofuran94%
(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
1279691-36-9

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

benzyl bromide
100-39-0

benzyl bromide

(2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-2-methoxytetrahydro-2H-pyran

(2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-2-methoxytetrahydro-2H-pyran

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide87%
(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
1279691-36-9

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

empagliflozin
864070-44-0

empagliflozin

Conditions
ConditionsYield
With triethylsilane; aluminum (III) chloride In dichloromethane; acetonitrile82.5%
With triethylsilane; aluminum (III) chloride In dichloromethane; acetonitrile at -5 - 10℃; for 2h; Large scale;78%
Stage #1: (2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol With aluminum (III) chloride In dichloromethane; acetonitrile at 5℃; for 0.5h; Large scale;
Stage #2: With triethylsilane In dichloromethane; acetonitrile at 10℃; for 2h; Large scale;
78%
(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
1279691-36-9

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

allyl bromide
106-95-6

allyl bromide

(2S,3R,4S,5R,6R)-3,4,5-tris(allyloxy)-6-((allyloxy)methyl)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-2-methoxytetrahydro-2H-pyran

(2S,3R,4S,5R,6R)-3,4,5-tris(allyloxy)-6-((allyloxy)methyl)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-2-methoxytetrahydro-2H-pyran

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide82%
(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
1279691-36-9

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

A

(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)tetrahydro-2H-pyran-3,4,5-trityl triacetate

(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)tetrahydro-2H-pyran-3,4,5-trityl triacetate

B

C31H35ClO11

C31H35ClO11

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide
2.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane; acetonitrile / 0.5 h / 15 - 20 °C
2.2: 90 °C
View Scheme
Multi-step reaction with 2 steps
1: triethylamine; dmap / tetrahydrofuran
2: aluminum (III) chloride; triethylsilane / dichloromethane; acetonitrile / 0.5 h / 15 - 20 °C
View Scheme
(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
1279691-36-9

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

A

2,3,4,6-tetra-O-benzyl-1-deoxy-1-((S)-(4-chloro-3-(4-(tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-β-D-glucopyranose

2,3,4,6-tetra-O-benzyl-1-deoxy-1-((S)-(4-chloro-3-(4-(tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-β-D-glucopyranose

B

C51H51ClO7

C51H51ClO7

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide
2: aluminum (III) chloride; triethylsilane / dichloromethane; acetonitrile / 0.5 h / 15 - 20 °C
View Scheme
(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
1279691-36-9

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

A

1-chloro-4-(2,3,4,6-tetra-O-allyl-D-glucopyranos-1-yl)-2-(4-(S)-tetrahydrofuran-3-yloxy-benzyl)-benzene

1-chloro-4-(2,3,4,6-tetra-O-allyl-D-glucopyranos-1-yl)-2-(4-(S)-tetrahydrofuran-3-yloxy-benzyl)-benzene

B

C35H43ClO7

C35H43ClO7

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide
2: triethylsilane; boron trifluoride diethyl etherate / dichloromethane; acetonitrile / 0.5 h / 15 - 20 °C
View Scheme
(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
1279691-36-9

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

C23H27ClO7

C23H27ClO7

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: boron trifluoride diethyl etherate / water
2: triethylsilane
View Scheme
(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
1279691-36-9

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

C23H27ClO8

C23H27ClO8

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In water
(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
1279691-36-9

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

(2R,3R,4R,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

(2R,3R,4R,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide
2.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane; acetonitrile / 0.5 h / 15 - 20 °C
2.2: 90 °C
View Scheme
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