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Hangzhou Think Chemical Co. Ltd

Methyl 1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-alpha-D-glucopyranoside CAS No.:714269-57-5 HANGZHOU THINK CHEMICAL CO., LTD. (THINKCHEM) is an integrative corporation of trade, research and contract manufacture. With about ten years

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

Xi'an Xszo Chem Co., Ltd.

1. Factory price and high quality must be guaranteed, base on 8 years of production and R&D experience2. Free samples will be provided,ensure specifications and quality are right for customer3. Customers will receive the most professional technical s

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

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-ethoxyphenyl)methyl]phenyl]-alpha-D-glucopyranoside

Cas:714269-57-5

Min.Order:1 Kilogram

FOB Price: $1.0 / 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-ethoxybenzyl)-phenyl]-α-D-glucopyranoside

Cas:714269-57-5

Min.Order:5 Kiloliter

FOB Price: $1.2 / 5.0

Type:Manufacturers

inquiry

Jinan Finer Chemical Co., Ltd

Product Description Product website: http://www.finerchem.com/pro01en/id/1693.html Product Name Methyl 1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-alpha-D-glucopyranoside

Methyl 1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-alpha-D-glucopyranoside

Cas:714269-57-5

Min.Order:1 Gram

FOB Price: $2.0

Type:Lab/Research institutions

inquiry

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.

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxyMethyl)-2-Methoxytetrahydro-2H-pyran-3,4,5-triol

Cas:714269-57-5

Min.Order:1 Kilogram

FOB Price: $0.9 / 1.0

Type:Lab/Research institutions

inquiry

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

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxyMethyl)-2-Methoxytetrahydro-2H-pyran-3,4,5-triol

Cas:714269-57-5

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Hebei Nengqian Chemical Import and Export Co., LTD

Our advantages: 1. All inquiries will be replied within 12 hours. 2. Dedication to quality, supply & service. 3. Strictly on selecting raw materials. 4. Reasonable & competitive price, fast lead time. 5. Sample is available for your eva

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxyMethyl)-2-Methoxytetrahydro-2H-pyran-3,4,5-triol

Cas:714269-57-5

Min.Order:1 Kilogram

FOB Price: $9.0 / 99.0

Type:Trading Company

inquiry

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

Hebei Sankai Chemical Technology Co., Ltd

1. Product advantages High purity, all above 98.5%, no impurities after dissolution We will test each batch to ensure quality OEM and private brand services designed for free Various cap colors available We can also provide MT1 peptide powder 2. Fact

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

a-D-Glucopyranoside, methyl 1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-

Cas:714269-57-5

Min.Order:1 Kilogram

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

a-D-Glucopyranoside, methyl 1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-

Cas:714269-57-5

Min.Order:0

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:By

Methyl 1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-alpha-D-glucopyranoside

Cas:714269-57-5

Min.Order:100 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Hangzhou Keyingchem Co.,Ltd

Hangzhou KeyingChem Co., Ltd. exported this product to many countries and regions at best price. If you are looking for the material’s manufacturer or supplier in China, KeyingChem is your best choice. Pls contact with us freely for getting det

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxyMethyl)-2-Methoxytetrahydro-2H-pyran-3,4,5-triol

Cas:714269-57-5

Min.Order:0 Metric Ton

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

714269-57-5

Cas:714269-57-5

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

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

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxyMethyl)-2-Methoxytetrahydro-2H-pyran-3,4,5-triol

Cas:714269-57-5

Min.Order:4 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Saiwante (shanghai) New Material Technology Co., Ltd.

Boiling Point:609.6±55.0 °C(Predicted) PKA:12.59±0.70(Predicted) PSA:108.61000 Density:1.39±0.1 g/cm3 (20 oC 760 Torr) LogP:1.60250 Storage Temp.:2-8°C Solubility.:Acetonitrile (Slightly), DMSO (Slightly), M

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

Hangzhou Lingrui Chemical Co.,Ltd.

Methyl 1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-alpha-D-glucopyranosideAppearance:White powder Storage:cool and seal Package:according to customers' requirements Application:Dapagliflozin intermediate Transportation:By air(EMS or EUB or FedEx

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

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxyMethyl)-2-Methoxytetrahydro-2H-pyran-3,4,5-triol

Cas:714269-57-5

Min.Order:100 Gram

FOB Price: $100.0 / 2000.0

Type:Lab/Research institutions

inquiry

Siwei Development Group Ltd.

Product name: Methyl 1-C-[4-Chloro-3-(4-Ethoxybenzyl)Phenyl]-Alpha-D-Glucopyranoside CAS No.:714269-57-5 Molecule Formula:C22H27ClO7 Molecule Weight:438.89 Purity: 99% Package: 25kg/drum Description:White powder Manufacture Standards:Enterpris

High Quality Methyl 1-C-[4-Chloro-3-(4-Ethoxybenzyl)Phenyl]-Alpha-D-Glucopyranoside in stock

Cas:714269-57-5

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Hangzhou Huarong Pharm Co., Ltd.

Huarong Industrial Group Limited established since 2006 , has been actively developing specialty products for Finished Dosages, APIs, Intermediates, and Fine chemicals markets in North America, Europe, Korea, Japan, Mid-East and all over the World.

Methyl 1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-alpha-D-glucopyranoside

Cas:714269-57-5

Min.Order:1 Gram

FOB Price: $1.0 / 2.0

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,

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxyMethyl)-2-Methoxytetrahydro-2H-pyran-3,4,5-triol

Cas:714269-57-5

Min.Order:1 Kilogram

Negotiable

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,

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

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

Xiamen Hisunny Chemical Co.,Ltd

Best quality & Attractive price & Professional service; Trial & Pilot & CommercialHisunny Chemical is a leading manufacturer and supplier of chemicals in China. We develop produce and distribute high quality intermediates, special chemicals and OLED

Methyl 1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-alpha-D-glucopyranoside

Cas:714269-57-5

Min.Order:0

Negotiable

Type:Trading Company

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

Synthetic route

1-chloro-2-(4-ethoxybenzyl)-4-iodobenzene
1103738-29-9

1-chloro-2-(4-ethoxybenzyl)-4-iodobenzene

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one
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-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
714269-57-5

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol

Conditions
ConditionsYield
Stage #1: 1-chloro-2-(4-ethoxybenzyl)-4-iodobenzene; (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one With TurboGrignard In tetrahydrofuran at -30 - -20℃; for 1h; Inert atmosphere;
Stage #2: With methanesulfonic acid In tetrahydrofuran; methanol at -10 - 30℃; for 2h; Inert atmosphere;
81.8%
methanesulfonic acid
75-75-2

methanesulfonic acid

C33H56ClO7Si4(1-)*Li(1+)

C33H56ClO7Si4(1-)*Li(1+)

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
714269-57-5

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol

Conditions
ConditionsYield
In methanol at 20℃; for 10h;81.4%
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

C18H42O6Si4

C18H42O6Si4

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
714269-57-5

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane; toluene at -78 - -65℃; for 2h; Inert atmosphere;78.6%
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one
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-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
714269-57-5

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol

Conditions
ConditionsYield
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With sec.-butyllithium In tetrahydrofuran; cyclohexane at -78 - -68℃; for 1h;
Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; n-heptane; cyclohexane at -78 - -68℃; for 30h;
78.3%
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran; hexane; toluene at -78℃; for 1h; Large scale;
Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one With n-butyllithium In tetrahydrofuran; hexane; toluene at -78℃; for 3h; Large scale;
78%
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran; hexane; toluene at -78℃; for 1h; Inert atmosphere; Industrial scale;
Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one With methanesulfonic acid In tetrahydrofuran; methanol; hexane; toluene at -78 - 40℃; for 14h; Industrial scale;
78%
Multi-step reaction with 2 steps
1.1: N,N,N',N'',N'''-pentamethyldiethylenetriamine; n-butyllithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere
1.2: 2 h / -78 °C / Inert atmosphere
2.1: methanol / 10 h / 20 °C
View Scheme
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

methanesulfonic acid
75-75-2

methanesulfonic 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-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
714269-57-5

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol

Conditions
ConditionsYield
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran; hexane; toluene at -78℃; for 1h; Inert atmosphere; Large scale;
Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane; toluene at -78℃; for 3h; Large scale;
Stage #3: methanesulfonic acid In methanol at 0 - 40℃; for 11h; Large scale;
78%
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

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,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
714269-57-5

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane; toluene at -78 - -65℃; for 2h; Inert atmosphere;77.3%
methanol
67-56-1

methanol

(2S,3R,4S,5R,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-3,4,5-tris(trimethylsilyloxy)-6-(trimethylsilyloxymethyl)tetrahydropyran-2-ol

(2S,3R,4S,5R,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-3,4,5-tris(trimethylsilyloxy)-6-(trimethylsilyloxymethyl)tetrahydropyran-2-ol

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
714269-57-5

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol

Conditions
ConditionsYield
With toluene-4-sulfonic acid at 20℃; for 12h; Inert atmosphere;71.6%
With n-butyllithium; toluene-4-sulfonic acid at 20℃; for 12h;141.5 g
(2S,3R,4S,5R,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-3,4,5-tris(trimethylsilyloxy)-6-(trimethylsilyloxymethyl)tetrahydropyran-2-ol

(2S,3R,4S,5R,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-3,4,5-tris(trimethylsilyloxy)-6-(trimethylsilyloxymethyl)tetrahydropyran-2-ol

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
714269-57-5

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol

Conditions
ConditionsYield
With toluene-4-sulfonic acid In methanol at 20 - 30℃; for 12h; Inert atmosphere;71.6%
methanol
67-56-1

methanol

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
714269-57-5

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol

Conditions
ConditionsYield
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran; hexane; toluene at -30℃;
Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane; toluene at -30 - -24℃;
Stage #3: methanol In tetrahydrofuran; hexane; toluene at -10 - 35℃; for 23h; Acidic conditions;
(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one
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-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
714269-57-5

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: n-butyllithium / tetrahydrofuran; hexane / 0.67 h / -78 °C / Inert atmosphere
1.2: 5 h / -78 °C / Inert atmosphere
2.1: toluene-4-sulfonic acid / 12 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1.1: n-butyllithium / tetrahydrofuran; hexane / 0.67 h / -78 °C
1.2: 5 h / -78 °C
2.1: n-butyllithium; toluene-4-sulfonic acid / 12 h / 20 °C
View Scheme
methanol
67-56-1

methanol

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one
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-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
714269-57-5

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol

Conditions
ConditionsYield
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran; hexane; toluene at -65℃;
Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane; toluene at -65℃; for 2h;
Stage #3: methanol With hydrogenchloride; water In tetrahydrofuran; hexane; toluene at 20℃;
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene; (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one With n-butyllithium In tetrahydrofuran at -85 - -70℃; for 2h; Inert atmosphere;
Stage #2: methanol With methanesulfonic acid In tetrahydrofuran at -75 - 15℃; for 18h; Inert atmosphere;
With n-butyllithium; methanesulfonic acid In tetrahydrofuran; toluene at -15 - 5℃; for 0.0113889h;
2-chloro-5-iodobenzoylchloride
281652-58-2

2-chloro-5-iodobenzoylchloride

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
714269-57-5

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: aluminum (III) chloride / dichloromethane / 0.5 h / -3 - 5 °C
1.2: 12 h / 0 - 25 °C
1.3: polymethylhydrosiloxane (PMHS) / 16 h / 30 °C
2.1: TurboGrignard / tetrahydrofuran / 1.5 h / -5 - 0 °C / Inert atmosphere
2.2: 1 h / -5 - 0 °C
2.3: 16 h / -10 - 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: aluminum (III) chloride / dichloromethane / 2 h / 0 - 5 °C
1.2: polymethylhydrosiloxane / 26 h / 25 - 30 °C
2.1: TurboGrignard / tetrahydrofuran / 0.67 h / -60 - -50 °C / Inert atmosphere
2.2: 5.67 h / -60 - -50 °C / Inert atmosphere
2.3: 18 h / -10 - 15 °C
View Scheme
Phenetole
103-73-1

Phenetole

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
714269-57-5

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 15 h / 25 - 30 °C
1.2: 2 h / 0 - 10 °C
2.1: aluminum (III) chloride; sodium tetrahydroborate / Dimethyl ether / 30 h / 0 - 65 °C
3.1: n-butyllithium / tetrahydrofuran; toluene / 1 h / -75 - -60 °C
3.2: 3 h / -75 - -60 °C
3.3: 18 h / -75 - 25 °C
View Scheme
D-Glucono-1,5-lactone
90-80-2

D-Glucono-1,5-lactone

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
714269-57-5

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 4-methyl-morpholine / tetrahydrofuran / 17 h / 5 - 25 °C / Inert atmosphere; Large scale
2.1: TurboGrignard / tetrahydrofuran / 0.67 h / -60 - -50 °C / Inert atmosphere
2.2: 5.67 h / -60 - -50 °C / Inert atmosphere
2.3: 18 h / -10 - 15 °C
View Scheme
Multi-step reaction with 3 steps
1.1: 4-methyl-morpholine / tetrahydrofuran / 10 h / 20 °C / Inert atmosphere
2.1: n-butyllithium / tetrahydrofuran; hexane / 0.67 h / -78 °C / Inert atmosphere
2.2: 5 h / -78 °C / Inert atmosphere
3.1: toluene-4-sulfonic acid / 12 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1.1: 4-methyl-morpholine / tetrahydrofuran / 8 h / 20 - 30 °C / Inert atmosphere
2.1: n-butyllithium / tetrahydrofuran; hexane / 0.67 h / -78 °C / Inert atmosphere
2.2: 5 h / -78 °C / Inert atmosphere
3.1: toluene-4-sulfonic acid / methanol / 12 h / 20 - 30 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1.1: 4-methyl-morpholine / tetrahydrofuran / 10 h / 20 °C
2.1: n-butyllithium / tetrahydrofuran; hexane / 0.67 h / -78 °C
2.2: 5 h / -78 °C
3.1: n-butyllithium; toluene-4-sulfonic acid / 12 h / 20 °C
View Scheme
2-chloro-5-iodobenzoic acid
19094-56-5

2-chloro-5-iodobenzoic acid

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
714269-57-5

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 16.17 h / 10 - 25 °C
2.1: aluminum (III) chloride / dichloromethane / 0.5 h / -3 - 5 °C
2.2: 12 h / 0 - 25 °C
2.3: polymethylhydrosiloxane (PMHS) / 16 h / 30 °C
3.1: TurboGrignard / tetrahydrofuran / 1.5 h / -5 - 0 °C / Inert atmosphere
3.2: 1 h / -5 - 0 °C
3.3: 16 h / -10 - 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 16 h / 10 - 25 °C
2.1: aluminum (III) chloride / dichloromethane / 2 h / 0 - 5 °C
2.2: polymethylhydrosiloxane / 26 h / 25 - 30 °C
3.1: TurboGrignard / tetrahydrofuran / 0.67 h / -60 - -50 °C / Inert atmosphere
3.2: 5.67 h / -60 - -50 °C / Inert atmosphere
3.3: 18 h / -10 - 15 °C
View Scheme
methanol
67-56-1

methanol

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol
960404-86-8

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
714269-57-5

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran at -10 - 15℃; for 18h; Temperature;
With methanesulfonic acid In neat (no solvent) at 20℃; for 6h; Inert atmosphere;
methanol
67-56-1

methanol

1-chloro-2-(4-ethoxybenzyl)-4-iodobenzene
1103738-29-9

1-chloro-2-(4-ethoxybenzyl)-4-iodobenzene

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one
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-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
714269-57-5

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol

Conditions
ConditionsYield
Stage #1: 1-chloro-2-(4-ethoxybenzyl)-4-iodobenzene With TurboGrignard In tetrahydrofuran at -5 - 0℃; for 1.5h; Inert atmosphere;
Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one With TurboGrignard In tetrahydrofuran; n-heptane at -5 - 0℃; for 1h;
Stage #3: methanol With hydrogenchloride In tetrahydrofuran; n-heptane; water at -10 - 20℃; for 16h; Concentration; Temperature;
Stage #1: 1-chloro-2-(4-ethoxybenzyl)-4-iodobenzene With TurboGrignard In tetrahydrofuran at -60 - -50℃; for 0.666667h; Inert atmosphere;
Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; n-heptane at -60 - -50℃; for 5.66667h; Inert atmosphere;
Stage #3: methanol With hydrogenchloride; water In tetrahydrofuran at -10 - 15℃; for 18h; Temperature; Time;
C34H59ClO7Si4
1528636-28-3

C34H59ClO7Si4

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
714269-57-5

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol

Conditions
ConditionsYield
With water; sodium hydroxide In tetrahydrofuran; hexane; toluene for 1h;7.69 kg
(3R,4S,5R,6R)-3,4,5-tris(trimethylsilyloxy)-6-((trimethylsilyloxy)methyl)tetrahydro-2H-pyran-2-one

(3R,4S,5R,6R)-3,4,5-tris(trimethylsilyloxy)-6-((trimethylsilyloxy)methyl)tetrahydro-2H-pyran-2-one

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
714269-57-5

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: n-butyllithium / tetrahydrofuran; hexane / 0.67 h / -78 °C / Inert atmosphere
1.2: 5 h / -78 °C / Inert atmosphere
2.1: toluene-4-sulfonic acid / methanol / 12 h / 20 - 30 °C / Inert atmosphere
View Scheme
D-glucono-1,4-lactone
1198-69-2

D-glucono-1,4-lactone

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
714269-57-5

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-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
Multi-step reaction with 2 steps
1: triethylamine / tetrahydrofuran / 1 h / -10 - 45 °C
2: n-butyllithium / tetrahydrofuran; toluene; hexane / 2 h / -78 - -65 °C / Inert atmosphere
View Scheme
1-chloro-2-(4-ethoxybenzyl)-4-iodobenzene
1103738-29-9

1-chloro-2-(4-ethoxybenzyl)-4-iodobenzene

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one
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,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
714269-57-5

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol

B

C21H27ClO7

C21H27ClO7

Conditions
ConditionsYield
Stage #1: 1-chloro-2-(4-ethoxybenzyl)-4-iodobenzene With TurboGrignard In tetrahydrofuran at -5 - 0℃; for 1h; Inert atmosphere;
Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran at 5℃; for 3h; Inert atmosphere;
Stage #3: With hydrogenchloride; methanol In tetrahydrofuran Inert atmosphere;
5-bromo-2-chlorobenzoic acid
21739-92-4

5-bromo-2-chlorobenzoic acid

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
714269-57-5

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 15 h / 25 - 30 °C
1.2: 2 h / 0 - 10 °C
2.1: aluminum (III) chloride; sodium tetrahydroborate / Dimethyl ether / 30 h / 0 - 65 °C
3.1: n-butyllithium / tetrahydrofuran; toluene / 1 h / -75 - -60 °C
3.2: 3 h / -75 - -60 °C
3.3: 18 h / -75 - 25 °C
View Scheme
(5-bromo-2-chlorophenyl)(4-ethyloxyphenyl)methanone
461432-22-4

(5-bromo-2-chlorophenyl)(4-ethyloxyphenyl)methanone

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
714269-57-5

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: aluminum (III) chloride; sodium tetrahydroborate / Dimethyl ether / 30 h / 0 - 65 °C
2.1: n-butyllithium / tetrahydrofuran; toluene / 1 h / -75 - -60 °C
2.2: 3 h / -75 - -60 °C
2.3: 18 h / -75 - 25 °C
View Scheme
3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-one

3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-one

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
714269-57-5

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 4-methyl-morpholine / tetrahydrofuran / 15 h / 0 - 40 °C
2.1: n-butyllithium / tetrahydrofuran; toluene / 1 h / -75 - -60 °C
2.2: 3 h / -75 - -60 °C
2.3: 18 h / -75 - 25 °C
View Scheme
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

3,4,5-tris[(trimethylsilyl)oxy]-6-{[(trimethylsilyl)oxy]methyl}-tetrahydro-2H-pyran-2-one

3,4,5-tris[(trimethylsilyl)oxy]-6-{[(trimethylsilyl)oxy]methyl}-tetrahydro-2H-pyran-2-one

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
714269-57-5

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol

Conditions
ConditionsYield
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran; toluene at -75 - -60℃; for 1h;
Stage #2: 3,4,5-tris[(trimethylsilyl)oxy]-6-{[(trimethylsilyl)oxy]methyl}-tetrahydro-2H-pyran-2-one In tetrahydrofuran; toluene at -75 - -60℃; for 3h;
Stage #3: With methanesulfonic acid In tetrahydrofuran; methanol; toluene at -75 - 25℃; for 18h;
82 g
2-chloro-benzaldehyde
89-98-5

2-chloro-benzaldehyde

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
714269-57-5

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: N-Bromosuccinimide / dichloromethane / 10.5 h / 5 °C / Large scale
2.1: sodium tetrahydroborate / ethanol / 4 h / 20 °C / Large scale
3.1: thionyl chloride / 3 h / 70 °C / Large scale
4.1: aluminum (III) chloride / ethyl acetate / 9 h / 78 °C / Cooling with ice; Large scale
5.1: n-butyllithium / tetrahydrofuran; toluene; hexane / 1 h / -78 °C / Large scale
5.2: 3 h / -78 °C / Large scale
View Scheme
2-chloro-5-bromobenzaldehyde
189628-37-3

2-chloro-5-bromobenzaldehyde

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
714269-57-5

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sodium tetrahydroborate / ethanol / 4 h / 20 °C / Large scale
2.1: thionyl chloride / 3 h / 70 °C / Large scale
3.1: aluminum (III) chloride / ethyl acetate / 9 h / 78 °C / Cooling with ice; Large scale
4.1: n-butyllithium / tetrahydrofuran; toluene; hexane / 1 h / -78 °C / Large scale
4.2: 3 h / -78 °C / Large scale
View Scheme
5-bromo-2-chlorobenzyl alcohol
149965-40-2

5-bromo-2-chlorobenzyl alcohol

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
714269-57-5

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: thionyl chloride / 3 h / 70 °C / Large scale
2.1: aluminum (III) chloride / ethyl acetate / 9 h / 78 °C / Cooling with ice; Large scale
3.1: n-butyllithium / tetrahydrofuran; toluene; hexane / 1 h / -78 °C / Large scale
3.2: 3 h / -78 °C / Large scale
View Scheme
4-bromo-1-chloro-2-(chloromethyl)benzene

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

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
714269-57-5

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-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 / 1 h / -78 °C / Large scale
2.2: 3 h / -78 °C / Large scale
View Scheme
4-bromo-aniline
106-40-1

4-bromo-aniline

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
714269-57-5

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: water; methanol / 5 h / 20 °C / Cooling with ice; Large scale
2.1: aluminum (III) chloride / ethyl acetate / 8 h / Cooling with ice; Reflux; Large scale
3.1: hydrogenchloride / water; methanol / 6 h / 80 °C / Large scale
4.1: hydrogenchloride; sodium nitrite / water / 3 h / -5 - 0 °C / Large scale
4.2: 4 h / 20 - 80 °C / Large scale
5.1: n-butyllithium / tetrahydrofuran; toluene; hexane / 1 h / -78 °C / Inert atmosphere; Large scale
5.2: 3 h / -78 °C / Large scale
5.3: 11 h / 0 - 40 °C / Large scale
View Scheme
Multi-step reaction with 5 steps
1.1: water; methanol / 5.5 h / 20 °C / Cooling with ice; Industrial scale
2.1: hydrogen fluoride / ethyl acetate / 8.5 h / Cooling with ice; Industrial scale
3.1: hydrogenchloride / water; methanol / 6 h / 80 °C / Industrial scale
4.1: hydrogenchloride; sodium nitrite / water / 3 h / -5 °C / Industrial scale
4.2: 4 h / 20 - 80 °C / Industrial scale
5.1: n-butyllithium / tetrahydrofuran; toluene; hexane / 1 h / -78 °C / Inert atmosphere; Industrial scale
5.2: 14 h / -78 - 40 °C / Industrial scale
View Scheme

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